ZA200506398B - Optically active bisoxazoline, compounds, process for production of the same and use thereof - Google Patents
Optically active bisoxazoline, compounds, process for production of the same and use thereof Download PDFInfo
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- ZA200506398B ZA200506398B ZA200506398A ZA200506398A ZA200506398B ZA 200506398 B ZA200506398 B ZA 200506398B ZA 200506398 A ZA200506398 A ZA 200506398A ZA 200506398 A ZA200506398 A ZA 200506398A ZA 200506398 B ZA200506398 B ZA 200506398B
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- naphthyl
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- 150000001875 compounds Chemical class 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- -1 diamide compound Chemical class 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 239000005749 Copper compound Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 150000001880 copper compounds Chemical class 0.000 claims description 2
- 150000001414 amino alcohols Chemical class 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 150000004699 copper complex Chemical class 0.000 claims 4
- NSTPXGARCQOSAU-UHFFFAOYSA-N N-Formyl-Phenylalanine Natural products O=CNC(C(=O)O)CC1=CC=CC=C1 NSTPXGARCQOSAU-UHFFFAOYSA-N 0.000 claims 3
- NSTPXGARCQOSAU-VIFPVBQESA-N N-formyl-L-phenylalanine Chemical compound O=CN[C@H](C(=O)O)CC1=CC=CC=C1 NSTPXGARCQOSAU-VIFPVBQESA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 239000012320 chlorinating reagent Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 71
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 43
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 36
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 28
- 239000001294 propane Substances 0.000 description 22
- 125000003003 spiro group Chemical group 0.000 description 22
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 17
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 14
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 13
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 7
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 6
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 6
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 6
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 6
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 150000001942 cyclopropanes Chemical class 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- BEQDKWKSUMQVMX-UHFFFAOYSA-N 2,4-dimethyl-4,5-dihydro-1,3-oxazole Chemical compound CC1COC(C)=N1 BEQDKWKSUMQVMX-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical group CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000011982 enantioselective catalyst Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Electroluminescent Light Sources (AREA)
Description
2b 3 ERS y 1
OPTICALLY ACTIVE BISOXAZOLINE COMPOUNDS, PROCESS FOR
PRODUCTION OF THE SAME AND USE THEREOF
The present invention relates to optically active bisoxazoline compounds, process for production of the same and use thereof.
Methods for producing optically active cyclopropane compounds, which are very important compounds as synthesis intermediates of agricultural chemicals such as synthesized pyrethroid type insecticides, pharmaceuticals, etc., and whose representative example is (+)-2,2-dimethyl-3-(2- methyl-l-propenyl)cyclopropanecarboxylic acid, from prochiral olefins have been known as an asymmetric reaction using an optically active bisoxazoline compound as a ligand (e.g. JP 11-171874 A, Tetrahedron Lett., 32, 7373 (1991)).
These methods are relatively good in the diastereoselectivity (trans-isomer/cis-isomer ratio) and enantioselectivity. However, from an industrial viewpoint, it 1s desired to further improve the yield of the desired optically active cyclopropane compounds.
Disclosure of the Invention i
According to the present invention, an optically active bisoxazoline compound having naphthyl group as an asymmetric synthesis catalyst component can be easily obtained, and an optically active compound can be obtained at a high yield by using an industrially advantageous asymmetric catalyst comprising the optically active bisoxazoline compound and a copper compound.
That is, the present invention provides an optically active bisoxazoline compound represented by the formula (1):
RA RS
R! = Rr! > Lose 2
R® R® wherein R- and R? are the same, and each represents a Ci-¢ alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted phenyl group, or R! and
R? are bonded each other together with the carbon atom of the oxazoline ring to which they are bonded to form a ring;
Rr? represents a substituted or unsubstituted naphthyl group (preferably a l-naphthyl group or a 2-naphthyl group); R’ and R’> are the same, and each represents a hydrogen atom or a Ci-¢ alkyl group, or R® and R® are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms; and *
represents an asymmetric center; a process for production of the same and use thereof.
Best Mode for Carrying Out the present invention
First, the optically active bisoxazoline compound represented by the formula (1) (hereinafter, simply referred to as the optically active bisoxazoline compound (1)), which is a novel compound, will be illustrated.
Examples of the C;_¢ alkyl group represented by R! and
R° include straight chain or branched alkyl groups such as a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n- pentyl, and n-hexyl group, and as the ring formed by bonding R' and R? each other together with the carbon atom of the oxazoline ring to which they are bonded, cycloalkyl rings having 3 to 7 carbon atoms can be exemplified.
Examples of the cycloalkyl ring include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring.
Examples of the substituted or unsubstituted phenyl group represented by R' and R? include an unsubstituted phenyl group; a phenyl group substituted with a Cj-¢ alkyl such as a 3-methylphenyl and 4-methylphenyl group; and a phenyl group substituted with a C:.¢ alkoxy group(e.g. a methoxy, ethoxy, propoxy, butoxy, pentyloxy, and hexyloxy group) such as a 2-methoxyphenyl, 3-methoxyphenyl, and 4-
methoxyphenyl group.
As the substituted or unsubstituted aralkyl group, there is, for example, a Cj;-¢ alkyl group substituted with the above substituted or unsubstituted aryl group.
Examples thereof include a benzyl, 2-methylbenzyl, 3- methylbenzyl, 4-methylbenzyl, 2-methoxybenzyl, 3- methoxybenzyl, 4-methoxybenzyl, l-naphthylmethyl, and 2- naphthylmethyl group.
In the formula representing the optically active bisoxazoline compound (1), as the substituted or unsubstituted naphthyl group represented by R>, in addition to an unsubstituted l-naphthyl or 2-naphtyl group, there are, for example, a l-naphthyl or 2-naphtyl group substituted with at least one C;_¢ alkyl or Ci.¢ alkoxy group.
Examples of the C;.¢ alkyl or Ci.¢ alkoxy group include those exemplified with respect to the substituent R!' or RZ.
Specifically, there are, for example, a 4-fluoro-l-naphthyl, 2-methyl-l-naphthyl, 4-methyl-l-naphthyl, 2-methoxy-1- naphthyl, 2-ethoxy-l-naphthyl, 4-methoxy-l-naphthyl, 2,4- dimethoxy-l-naphthyl, 2-naphthyl, 7-methyl-2-naphthyl, 1-n- propyl-2-naphthyl, 6-methoxy-2-naphthyl, and 3,8-dimethoxy- 2-naphthyl group. Among them, l-naphthyl and 2-naphthyl group are preferable.
Examples of the C:.¢ alkyl group represented by R* and
R® include a Ci.a alkyl group such as a methyl, ethyl, n-
d propyl, and isopropyl group, and a butyl, pentyl, and hexyl group. As the ring formed by bonding R! and R® each other together with the carbon atom of the oxazoline ring to which they are bonded , cycloalkyl rings having 3 to 6 carbon atoms can be exemplified. Examples of the cycloalkyl ring include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, and a cyclohexane ring.
Preferably, R* and R® represent a hydrogen atom, a Cj-3 alkyl group or a cycloalkyl ring having 3 to 6 carbon atoms formed by bonding R! and R® each other together with the carbon atom of the oxazoline ring to which they are bonded, and more preferably, they represent a C;_3 alkyl group.
In the bisoxazoline compounds represented by the formula (1), there are two asymmetric carbon atoms represented by * and the compounds wherein both asymmetric carbon atoms are (S), or (R) configurations are preferably used.
Specific examples of such optically active bisoxazoline compounds (1) include bis [2-[(48S)-(1- naphthyl) -5, 5-dimethyloxazoline] Jmethane, bis[2-[(4S)-(1- naphthyl) -5, 5-diethyloxazoline] Jmethane, bis[2-[(4S)-(1- naphthyl) -5, 5-di-n-propyloxazoline] Jmethane, bis[2-[(4S)- (l-naphthyl)-5, 5-di-n-butyloxazoline] methane, bis[2-[(49)- (l1-naphthyl) -5, 5-diisobutyloxazoline] Jmethane, bis[2-[(4S)-
J
(1-naphthyl)-5,5-di-n-pentyloxazoline] Jmethane, bis [2- [ (4S) -(l-naphthyl)-5,5-di-n-hexyloxazoline] methane, bis[2- [ (4S) -(1l-naphthyl)-5,5~-dibenzyloxazoline] Imethane, bis[2- ( (4S) -(1l-naphthyl)-5,5-di (2-methylbenzyl)oxazoline] Jmethane, bis{2-[(4S)-(1-naphthyl)-5,5-di (3- methylbenzyl)oxazoline] Jmethane, bis[2-[(4S)-(l-naphthyl)- 5,5~di (4-methylbenzyl)oxazoline] Jmethane, bis[2-[(4S)-(1- naphthyl) -5,5-di (2-methoxybenzyl) oxazoline] methane, bis[2- [(4S)-(l-naphthyl)-5,5-di (3- methoxybenzyl)oxazoline] methane, bis[2-[(4S)-(l-naphthyl)- 5,5-di(4-methoxybenzyl) oxazoline) Jmethane, bis[2-[(4S)-(1- naphthyl) -5,5-di (l1-naphthylmethyl) oxazoline] methane, bis[2-[(4S)~-(l-naphthyl)-5,5-di(2- naphthylmethyl)oxazoline] Jmethane, bis[2-[(4S)-(1- naphthyl) -5, 5-diphenyloxazoline] Jmethane, bis[2-[(4S)-(1- naphthyl) -5,5-di (3-methylphenyl) oxazoline] Jmethane, bis[2-[(4S)~-(l-naphthyl)-5, 5-di (4- methylphenyl)oxazoline] Jmethane, bis[2-[(4S)-(l-naphthyl)- 5,5-di (2-methoxyphenyl) oxazoline] lmethane, bis[2-[(4S)-(1- naphthyl) -5, 5-di (3-methoxyphenyl)oxazoline] Jmethane, bis[2- [ (4S) ~(l-naphthyl)-5,5-di (4- methoxyphenyl) oxazoline] Jmethane, bis{2-{spiro[(4S)-(1- naphthyl)oxazoline-5, 1’ -cyclopropane]) Jmethane, bis[2- [spiro[ (4S)-(l-naphthyl)oxazoline-5,1'- cyclobutane] ]]lmethane, bis[2-[spirol (4S)-(1-
naphthyl)oxazoline-5,1’ -cyclopentane] ] methane, bis [2- [spiro (4S)-(l-naphthyl)oxazoline-5,1’- cyclohexane] ] Jmethane, bis[2-[spiro[ (4S)-methyloxazoline- 5,1" ~cycloheptane] ] methane, 2,2-bis{2-[(4S)-(1l-naphthyl)-5, 5- dimethyloxazoline] lpropane, 2,2-bis[2-[(4S)-(l-naphthyl)- 5,5-diethyloxazoline] ]propane, 2,2-bis[2-[(4S)-(1- naphthyl) -5,5-di-n-propyloxazoline] propane, 2,2-bis[2- ((4S)~-(l-naphthyl)-5,5-di-n-butyloxazoline]]propane, 2,2- bis[2-[(4S)-(1l-naphthyl)-5,5-diisobutyloxazoline] propane, 2,2-bis[2-[(4S)-(l-naphthyl)-5,5-di-n- pentyloxazoline] ]propane, 2,2-bis[2-[(4S)-(l-naphthyl)-5,5- di-n-hexyloxazoline] ]propane, 2,2-[2-bis[2-(4S)-(1- naphthyl) -5, 5-dibenzyloxazoline] propane, 2,2-[2-bis[2- bis (4S) -(l-naphthyl)-5,5-di(2- methylbenzyl)oxazolinel propane, 2,2-bis{2-[(4S)-(1- naphthyl) -5, 5-di(3-methylbenzyl)oxazoline] ]propane, 2,2- bis[2-{(4S)-(1-naphthyl)-5,5-di (4- methylbenzyl) oxazoline] Jpropane, 2,2-bis{2-[(4S)-(1- naphthyl) -5, 5-di(2-methoxybenzyl)oxazoline] propane, 2,2- bis[(4S)-(l-naphthyl)-5,5-di(3- methoxybenzyl)oxazoline] ]propane, 2,2-bis[2-[(4S)~-(1- naphthyl) -5,5-di(4-methoxybenzyl)oxazoline] }propane, 2,2-pbis[2-[(45)~-(l-naphthyl)~-5,5-di(1- naphthylmethyl)oxazoline] ]propane, 2,2-bis{[(4S)-(1-
naphthyl) -5, 5-di (2-naphthylmethyl)oxazoline] ] propane, 2,2- bis[(4S)-(1-naphthyl)-5, 5-diphenyloxazoline]]propane, 2,2- bis[2-[(4S)-(1l-naphthyl)-5,5-di (3- methylphenyl)oxazoline]]propane, 2,2-bis[2-[(4S)-(1- naphthyl) -5, 5-di (4-methylphenyl) oxazoline] propane, 2,2-
bis[2-[(4S)~-(1l-naphthyl)-5,5-di (2-
methoxyphenyl) oxazoline] Jpropane, 2,2-bis[2-{(4S)-(1- naphthyl) -5, 5-di (3-methoxyphenyl) oxazoline] ]propane, 2,2- bis[2-[(4S)~-(1l-naphthyl)-5,5-di (4-
methoxyphenyl) oxazoline] ]propane, 2,2-bis[2-{spiro[(4S)-(1- naphthyl) oxazoline~5, 1’ ~cyclopropane]] lpropane, 2,2-bis[2- [spiro( (4S) -(1l-naphthyl)oxazoline=-5,1"- cyclobutane] ] ]propane, 2,2-bis[2-[spiro[(4S)-(1- naphthyl) oxazoline-5, 1’ -cyclopentane]]lpropane, 2,2-bis([2-
[spiro (4S) -(l-naphthyl)oxazoline-5,1’- cyclohexane] ] propane, 2,2-bis[2-[spiro[(4S)- methyloxazoline-5,1’ -cycloheptane]]] propane,
3,3-bis[2-[(48)~(l-naphthyl)-5, 5- dimethyloxazoline]]pentane, 3,3-bis[2-[(4S)-(1l-naphthyl)-
5,5-diethyloxazoline] ]pentane, 3,3-bis[2-[(4S)-(1- naphthyl) -5, 5-di-n-propyl-2-oxazoline] ] pentane, 3,3-bis[2- [(4S)-(l-naphthyl)-5,5-di-n-butyloxazoline] pentane, 3, 3- bis[2-[(4S)-(l-naphthyl)-5,5~diisobutyloxazoline] pentane, 3,3-bis[2-[(4S)-(1l-naphthyl)-5, 5-di-n-
pentyloxazoline]]pentane, 3,3-bis[2-[(4S)-(l-naphthyl)-5, 5-
di-n-hexyloxazoline] Jpentane, 3,3-bis[2-[(4S)-(1l-naphthyl)- 5,5-dibenzyloxazoline] pentane, 3,3-bis[2-bis[(48)-(1- naphthyl) -5,5~di(2-methylbenzyl) oxazoline] lpentane, 3,3- bis [2-[(4S)-(1l-naphthyl)-5,5-di (3-
methylbenzyl)oxazoline] ]pentane, 3,3-bis[2-[(4S)-(1- naphthyl) -5,5-di (4-methylbenzyl) oxazoline] Jpentane, 3, 3- bis{2-[(4S)-(l-naphthyl)-5,5-di (2- methoxybenzyl) oxazoline] Jpentane, 3,3-bis[(4S)-(1- naphthyl) -5, 5-di (3-methoxybenzyl) oxazoline] lpentane, 3,3-
bis[2-[(4S)-(1-naphthyl)-5,5-di(4- methoxybenzyl)oxazoline] pentane,
3,3-bis[2-[(4S)~-(l-naphthyl)-5,5-di(1- naphthylmethyl)oxazoline]]pentane, 3,3-[2-bis[(48)-(1- naphthyl) -5,5-di (2-naphthylmethyl) oxazoline] ]pentane, 3,3-~
[2-bis[(4S)-(1-naphthyl)-5, 5-diphenyloxazoline] ]pentane, 3,3-bis[2-[(4S)-(l-naphthyl)-5, 5~-di (3- methylphenyl) oxazoline] Jpentane, 3,3-bis[2-[(4S)-(1- naphthyl) -5, 5-di (4-methylphenyl) oxazoline] lpentane, 3, 3- bis[2-[(4S)-(1-naphthyl)-5, 5-di (2-
methoxyphenyl) oxazoline] ]pentane, 3,3-bis{[2-[(4S)-(1- naphthyl) -5, 5-di (3-methoxyphenyl) oxazoline] pentane, 3,3- bis[2-[(4S)-(1l-naphthyl)-5,5-di(4- methoxyphenyl) oxazoline] ]pentane, 3,3-bis[2-[spiro[ (4S)-(1- naphthyl)oxazoline-5, 1’ -cyclopropane]] ]pentane, 3,3-bis[2-
[spiro[(4S)-(l-naphthyl)oxazoline-5,1"-
cyclobutane] ] Jpentane, 3,3-bis[2-[spiro[ (4S)-(1- naphthyl) oxazoline-5,1’ -cyclopentane) ] pentane, 3,3-bis[2- [spiro[ (4S)-(l-naphthyl)oxazoline-5,1"'- cyclohexane] ]]lpentane, 3,3-bis[2-[spiro[(4S)- methyloxazoline-5,1’ -cycloheptane]]]pentane, 4,4-bis{2-{(4S8)-(l-naphthyl)-5,5- dimethyloxazoline] heptane, 4,4-bis[2-[(4S)-(l-naphthyl)-
S5,5-diethyl-2-oxazoline] heptane, 4,4-bis[2-[(4S)-(1- naphthyl) -5,5-di-n-propyloxazoline} heptane, 4,4-bis[2- [ (4S) -(l-naphthyl)~5, 5-di-n-butyloxazoline] lheptane, 4,4- bis[2-[(4S)-(1l-naphthyl)-5,5-diisobutyloxazoline] heptane, 4,4-bis[2-[(4S)-(l-naphthyl)-5,5-di-n- pentyloxazoline] ]heptane, 4,4-[2-bis[2-[(4S)-(1l-naphthyl)- 5,5-di-n-hexyloxazoline] heptane, 4,4-bis[2-[(4S8)-(1- naphthyl) -5, 5-dibenzyloxazoline) Jheptane, 4,4-bis[2- bis (4S) ~-(1l-naphthyl)-5,5-di (2- methylbenzyl)oxazoline] Jheptane, 4,4-bis[2-[(4S)-(1- naphthyl) -5,5-di (3-methylbenzyl) oxazoline] Jheptane, 4,4-[2- [ (4S) = (l-naphthyl)~-5, 5-di (4-methylbenzyl) oxazoline] heptane, 4,4-bis[2-[(4S)-(l-naphthyl)-5,5-di(2- methoxybenzyl) oxazoline] | heptane, 4,4-[2-bis[(4S)-(1- naphthyl) -5,5-di (3-methoxybenzyl) oxazoline] } heptane, 4,4- bis[2-[(4S)-(1l-naphthyl)-5,5-di (4- methoxybenzyl) oxazoline] ] heptane, 4,4-bis[2-[(4S)-(1l-naphthyl)-5,5-di(1-
pe naphthylmethyl)oxazoline]lheptane, 4,4-[2-bis[(4S)-(1- naphthyl) -5,5-di (2-naphthylmethyl) oxazoline] Jheptane, 4,4- bis[ (4S) - (1-naphthyl)-5, S-diphenyloxazoline] heptane, 4,4- bis[2~[(4S)-(l-naphthyl)-5,5-di (3-
methylphenyl)oxazoline] Jheptane, 4,4-bis[2-[(4S)-(1- naphthyl) -5,5-di (4-methylphenyl) oxazoline] heptane, 4, 4- bis[2-[(4S)-(1l-naphthyl)-5,5-di(2- methoxyphenyl)oxazoline] Jheptane, 4,4-bis[2-[(4S)-(1- naphthyl) -5, 5-di (3-methoxyphenyl)oxazoline] Jheptane, 4,4-
bis[2-[(4S)-(l-naphthyl)-5,5-di (4- methoxyphenyl) oxazoline] Jheptane, 4,4-bis[2-[spiro[ (4S)-(1- naphthyl) oxazoline-5,1’ -cyclopropane] ] J heptane, 4,4-bis[2- [spiro[(48)-(l-naphthyl)oxazoline-5,1"'- cyclobutane] ]lheptane, 4,4-bis[2-[spiro[(4S)-(1-
naphthyl) oxazoline-5,1’ -cyclopentane]] Jheptane, 4,4-bis[2- [spiro[ (43) -(l-naphthyl)oxazoline-5,1’- cyclohexane] ] heptane, 4,4-bis[2-[spiro[(4S)- methyloxazoline-5,1’ -cycloheptane]] heptane,
1,1-bis[2-[(4S)-(1-naphthyl)-5, 5-
dimethyloxazoline]]cyclopropane, 1,1-bis[2-[(4S)~-(1- naphthyl) -5, 5-diethyloxazoline] ] cyclopropane, 1,1l-bis[2-
[ (45) -(1-naphthyl)-5,5-di-n-propyl-2- oxazoline]]cyclopropane, 1,1-bis{2-[(4S)-(l-naphthyl)-5,5- di-n-butyloxazoline] ]Jcyclopropane, 1,1-bis{2-[(4S)-(1-
naphthyl) -5, 5-diisobutyloxazoline]]cyclopropane, 1,1l-bis[2-
[ (4S) - (1-naphthyl)-5,5-di-n-pentyloxazoline] ]cyclopropane, 1,1-bis[2-[(4S)-(1l-naphthyl)-5,5-di-n- hexyloxazoline] cyclopropane, 1,1-bis[2-[(4S)-(l-naphthyl)-
S,5-dibenzyloxazoline))cyclopropane, 1,1-bis[2-[(4S)-(1- naphthyl) -5,5-di(2-methylbenzyl) oxazoline] Jcyclopropane, 1,1-bis[2~[(4S)-(1l-naphthyl)-5,5-di (3- methylbenzyl)oxazoline] cyclopropane, 1,1-bis[2-[(4S)-(1- naphthyl) -5,5-di (4-methylbenzyl) oxazoline] ]cyclopropane, 1,1-bis{2-[(4S)~-(1-naphthyl)-5, 5-di (2- methoxybenzyl) oxazoline] ]Jcyclopropane, 1,1-bis[(4S)-(1- naphthyl) -5,5-di (3-methoxybenzyl) oxazoline] ]cyclopropane, 1,1-bis[2-[(4S)~-(l-naphthyl)-5,5-di (4- methoxybenzyl) oxazoline] Jcyclopropane, 1,1-bis[2-[(4S)~-(1l-naphthyl)-5,5-di (1- naphthylmethyl)oxazoline] Jcyclopropane, 1,1-bis[2-[(4S)-(1- naphthyl) -5,5-di (2-naphthylmethyl)oxazoline])cyclopropane, 1,1-bis{2-[(4S)-(l1-naphthyl)-5, 5- diphenyloxazoline]]cyclopropane, 1,1-bis[2-[(4S)-(1- naphthyl) -5,5-di (3-methylphenyl)oxazoline]]cyclopropane, 1,1-bis[2-[(4S)-(1-naphthyl)-5,5-di (4- methylphenyl) oxazoline] ]cyclopropane, 1,1-bis[2-[(4S)-(1- naphthyl) -5,5-di (2-methoxyphenyl) oxazoline] cyclopropane, 1,1-bis[2-[(4S)-(1-naphthyl)-5,5-di (3- methoxyphenyl)oxazoline] ]Jcyclopropane, 1,1-bis([2-[(4S)-(1- naphthyl) -5,5-di ({-methoxyphenyl) oxazoline] )}cyclopropane,
1l,1-bis(2~[spiro[(4S)-(l-naphthyl)oxazoline-5,1'- cyclopropane] ]lcyclopropane, 1,1l-bis[2-[spiro[(4S)-(1- naphthyl) oxazoline-5,1’ -cyclopentane]] cyclopropane, 1,1- bis[2-[spiro[ (4S)-methyloxazoline-5,1'~ cycloheptane]]lcyclopropane, 1,1-bis[2-[(4S)-(l-naphthyl)-5, 5- dimethyloxazoline] Jcyclobutane, 1,1-bis[2-[(4S)~-(1- naphthyl) -5,5-diethyloxazoline] ]cyclobutane, 1,1l-bis[2- [ (4S) -(l-naphthyl)-5,5-di~-n-propyl-2-oxazoline]]cyclobutane, 1,1-bis[2-[(4S)-(1-naphthyl)-5, 5-di-n- butyloxazoline]] cyclobutane, 1,1-bis([2-[(4S)-(l1-naphthyl)- 5,5-diisobutyloxazoline]]cyclobutane, 1,1-bis[2-[(4S)-(1- naphthyl) -5,5-di-n-pentyloxazoline])cyclobutane, 1, 1l-bis[2- [ (4S) = (1-naphthyl)-5,5-di~-n~-hexyloxazoline]]cyclobutane, 1,1-bis[2-[(4S)~-(1-naphthyl)-5, 5- dibenzyloxazoline) lcyclobutane, 1,1l-bis[2-[(48)-(1- naphthyl) -5, 5-di (2-methylbenzyl) oxazoline} )cyclobutane, 1,1-bis{2-[(4S)-(1-naphthyl)-5,5-di (3- methylbenzyl)oxazoline]]cyclobutane, 1,1-bis([2-[(4S)-(1- naphthyl) -5,5-di (4-methylbenzyl)oxazoline] cyclobutane, 1,1-bis[2-[(4S)-(1-naphthyl)-5, 5-di (2- methoxybenzyl)oxazoline]]cyclobutane, 1,1-bis[(4S)-(1- naphthyl) -5, 5-di (3-methoxybenzyl)oxazoline]]cyclobutane, 1,1-bis[2-[(4S)-(l-naphthyl)-5,5-d1i (4- methoxybenzyl)oxazoline]]cyclobutane,
Claims (16)
1. An optically active bisoxazoline compound represented by the formula (1): ge RS R'\_ Va Tx Mm TN Nk R® : R® R® wherein R! and R? are the same, and each represents a Cig alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted phenyl group, or R! and R?’ are bonded each other together with the carbon atom of the oxazoline ring to which they are bonded to form a ring; R3 represents a substituted or unsubstituted naphthyl group; R* and R® are the same and each represents a hydrogen atom or a Cj.¢ alkyl group, or RY and R® are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms; and * represents an asymmetric center.
2. The compound according to claim 1, wherein R! and R? are the same, and each represents a Cig alkyl group; R® represents a l-naphthyl group or a 2-naphthyl group; R? and R®> are the same, and each represents a hydrogen atom or a Ci-3 alkyl group, or R® and R®> are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms.
3. The compound according to claim 1 or 2, wherein the configurations of two asymmetric carbon atoms : represented by * are both (S), or ({(R).
4. A process for producing the optically active bisoxazoline compound represented by the formula (1) according to claim 1, which comprises reacting a Lewis acid with an optically active diamide compound represented by the formula (2): i Ke ul % x ’ "F “Yr R® 0 0 R® wherein R! and R? are the same, and each represents a Cj alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted phenyl group, or R} and R? are bonded each other together with the carbon atom to which they are bonded to form a ring; R’ represents a substituted or unsubstituted naphthyl group; R! and R® are the same, and each represents a hydrogen atom or a C;_g alkyl group, or R! and R® are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms; and * represents an asymmetric center.
5. The process according to claim 4, wherein the optically active diamide compound represented by the Corrected sheet: 28 February 2006 formula (2) is an optically active diamide compound obtained by reaction of an optically active amino alcohol represented by the formula (3): R3 Rr rt (3) HoN OH wherein R?, RZ, R?, and * are as defined in the formula (2) and a malonic acid compound represented by the formula (4): 0 0] RY R° wherein R' and R® are as defined in the formula (2); and 2 represents an alkoxy group or a halogen atom.
6. The optically active diamide compound represented by the formula (2) according to claim 4.
7. A process for producing the optically active diamide compound represented by the formula (2): ® ps y iN x y Va OS 0 Go TE. R® o) Q rR® wherein R' and R® are the same, and each represent a C, alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted phenyl group, or R! and R? are bonded each other together with the carbon atom of the oxazoline ring to which they are bonded to form a ring; Corrected sheet: 28 February 2006
R® represents a substituted or unsubstituted naphthyl group; R* and R’ are the same and each represents a hydrogen atom or a C;-¢ alkyl group, or R‘ and R® are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms; and * represents an asymmetric center, which comprises reacting an optically active amino alcohol represented by the formula (3): Rr R! Ht 3) HoN OH wherein R?, R?, R3, and * are as defined in the formula (2) with a malonic acid compound represented by the formula (4): 0 0 R* RK wherein R? and R®> are as defined in the formula (2); and Z represents an alkoxy group or a halogen atom.
8. An asymmetric copper complex produced from a copper compound and the optically active bisoxazoline compound represented by the formula (1):
Rr RS 1 Oo 0 1 XX Ts ® R Da N-_* R* R® R® wherein R! and R? are the same, and each represents a Cis alkyl group, a substituted or unsubstituted aralkyl group, Or a substituted or unsubstituted phenyl group, or R! and R? are bonded each other together with the carbon atom of the oxazoline ring to which they are bonded to form a ring; Rr? represents a substituted or unsubstituted naphthyl group; R® and R® are the same and each represents a hydrogen atom or a C;.¢ alkyl group, or R* and R® are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms; and * represents an asymmetric center.
9. The asymmetric copper complex according to claim 8, wherein R! and R? are the same, and each represents a Cj. 6 alkyl group; R’ represents a l-naphthyl group or a 2- naphthyl group; R! and R® are the same and each represent a hydrogen atom or a C;_.3 alkyl group, or R! and R® are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms,
10. The asymmetric copper complex according to claim 8, wherein the configurations of two asymmetric carbon atoms represented by * are both (S), or (R). Corrected sheet: 28 February 2006
11. A process for producing an optically active cyclopropane compound represented by the formula (7): rE R’ ) \/ g (0 CO:R™ wherein R®, R’, R®, and R® are the same or different, and independently represent a hydrogen atom, an alkyl group optionally substituted with a halogen atom, an alkenyl group optionally substituted with a halogen atom, a substituted or unsubstituted aryl or aralkyl group: provided that, when R® and R® are the same, R® and R’ are different from each other; and R!® represents a C;.¢ alkyl group, which comprises reacting a prochiral olefin represented by the formula (5): R® R’ = (5) R® R’ wherein RS, rR’, RS, and R® are as described above, with a diazoacetic acid ester represented by the formula (6): N,CHCO,R®? (6) wherein R!? is as defined above: in the presence of the asymmetric copper complex according to claim 8, 9, or 10.
12. An optically active amino alcohol represented by the formula (30): Corrected sheet: 28 February 2006
R R35 HO R35 Af NH 2 RAG LR eo) SNP R32 R33 wherein R*, R%?, R®, and R* are the same or different, and independently represent a hydrogen atom, a C;-¢ alkyl group, or a Ci-¢ alkoxy group; R®° represents a Cig alkyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted aralkyl group or two R*’ bonded to the same carbon atom are bonded together with the carbon atom to form a ring; and * represents an asymmetric carbon atom.
13. A process for producing an optically active naphthyl alcohol, which comprises reacting an amino alcohol represented by the formula (40): R35 HO R35 NH 34 N51 R™— —R 40 CIS “0 R32 R33 wherein R?!, R3?, R33, and R*! are the same or different and independently represent a hydrogen atom, a C;-¢ alkyl group, or a C;_¢ alkoxy group; rR? represents a C;-¢ alkyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted aralkyl group, or two R®> bonded to the same carbon atom are bonded together with the carbon atom to form a ring, with an optically active N- formylphenylalanine in a solvent to form diastereomeric salts of the optically active naphthyl alcohols and the optically active N-formylphenylalanine represented by the formula (30): RS HO R35 3ar= a R EX (30) R33 R32 wherein R3!, R32, R33, R34, and R®® are as described above, and * represents an asymmetric carbon atom, separating one diastereomeric salt from the other diastereomeric salt, and then treating the separated diastereomeric salt with an alkali.
14. The diastereomeric salt of the optically active amino alcohol represented by the formula (30) and the optically active N-formylphenylalanine according to claim
13.
15. A process for producing an amino alcohol represented by the formula (40):
,
R35 HO R3% _ ~,—NHa ~N R34— 2 p31 40 % | JR (40) R32 R33 wherein R3!, R32, R33, and R** are the same or different, and independently represent a hydrogen atom, a C;-¢ alkyl group, or a Ci_¢ alkoxy group; R*® represents a C;-¢ alkyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted aralkyl group or two R*® bonded to the same carbon atom are bonded together with the carbon atom to form a ring, which comprises the following steps (A) to (D) : (A) reacting a naphthylglycine compound represented by the formula (41): 0 HO _ +, —NHz J RC —+R3! (41) A Xs R33 R wherein R3!, R32, R33, and R** are the same or different and independently represent a hydrogen atom, a Ci.¢ alkyl group, or a Cj;.¢ alkoxy group, with a chlorinating agent and an alcohol represented by the formula (42): ROH (42)
wherein R® represents a Cig alkyl group, to obtain an amino acid ester hydrochloride represented by the formula (43): 0 R°0 NH, + HCI Zl WAS 34 N31 R™ = —R 43 Se I= (43) 32 R33 R wherein R**, R*?, R*®}, R?* ang R® are as described above,
(B) reacting the amino acid ester hydrochloride represented by the formula (43) obtained in the above step (A) with a compound represented by the formula (44):
(CnF2n+:CO) 20 (44) wherein n represents 1, 2 or 3, or the formula (45): CnF2n+1COX (45) wherein n is as described above; and X represents a chlorine atom, a bromine atom, or an iodine atom, in the presence of a tertiary amine to obtain a compound represented by the formula (46): 0 R°0 —NHCOC Fan, 1 pa Z pet Se A (46) R32 R33 wherein R*, R3¥, R®}, R¥, R® and n are as described above, (C) reacting the compound (46) obtained in the above step (B) with a compound represented by the formula (47):
R*Mgx’ (47) wherein R*® represents a C;.g alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted phenyl group; and X' represents a halogen atom, or a compound represented by the formula (48): X’ -Mg-R3®’ -Mg-X’ (48) wherein R3% represents a C;-¢ alkylene group and X’ is as defined above to obtain a compound represented by the formula (49): RS5 HO -R% 842° MN 31 R**— || "—R
NY." (49) RS2 R33 wherein R3!, R32, R33, R34, R* and n are as defined above, and (D) reacting the compound (49) obtained in the above step (C) with a base.
16. The compound represented by the formula (49) according to claim 15. Corrected sheet: 28 February 2006
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