JP2007513883A - 不斉合成法 - Google Patents
不斉合成法 Download PDFInfo
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- JP2007513883A JP2007513883A JP2006540371A JP2006540371A JP2007513883A JP 2007513883 A JP2007513883 A JP 2007513883A JP 2006540371 A JP2006540371 A JP 2006540371A JP 2006540371 A JP2006540371 A JP 2006540371A JP 2007513883 A JP2007513883 A JP 2007513883A
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- Prior art keywords
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- atom
- aryl
- alkyl
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- 238000011914 asymmetric synthesis Methods 0.000 title abstract description 12
- 239000003446 ligand Substances 0.000 claims abstract description 115
- 239000003054 catalyst Substances 0.000 claims abstract description 79
- 238000000034 method Methods 0.000 claims abstract description 73
- 125000004429 atom Chemical group 0.000 claims description 105
- 150000001875 compounds Chemical class 0.000 claims description 97
- 125000003118 aryl group Chemical group 0.000 claims description 90
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- -1 cyclic imines Chemical class 0.000 claims description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims description 78
- 239000001257 hydrogen Substances 0.000 claims description 76
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 71
- 125000001072 heteroaryl group Chemical group 0.000 claims description 61
- 238000007037 hydroformylation reaction Methods 0.000 claims description 46
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 41
- 125000002252 acyl group Chemical group 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 230000008569 process Effects 0.000 claims description 32
- 125000000524 functional group Chemical group 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 229910052698 phosphorus Inorganic materials 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- 150000001336 alkenes Chemical class 0.000 claims description 21
- 150000001299 aldehydes Chemical class 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 229910052723 transition metal Inorganic materials 0.000 claims description 17
- 150000003624 transition metals Chemical class 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 150000007942 carboxylates Chemical class 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052787 antimony Inorganic materials 0.000 claims description 12
- 229910052785 arsenic Inorganic materials 0.000 claims description 12
- 238000005810 carbonylation reaction Methods 0.000 claims description 12
- 238000011925 1,2-addition Methods 0.000 claims description 11
- 150000001450 anions Chemical class 0.000 claims description 11
- 230000006315 carbonylation Effects 0.000 claims description 11
- 150000001768 cations Chemical class 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 238000005669 hydrocyanation reaction Methods 0.000 claims description 11
- 238000005984 hydrogenation reaction Methods 0.000 claims description 11
- 125000004437 phosphorous atom Chemical group 0.000 claims description 11
- 150000002576 ketones Chemical class 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 238000006136 alcoholysis reaction Methods 0.000 claims description 7
- 238000005882 aldol condensation reaction Methods 0.000 claims description 7
- 238000006197 hydroboration reaction Methods 0.000 claims description 7
- 238000006317 isomerization reaction Methods 0.000 claims description 7
- 238000007098 aminolysis reaction Methods 0.000 claims description 6
- 150000002466 imines Chemical class 0.000 claims description 6
- 238000005649 metathesis reaction Methods 0.000 claims description 6
- 238000003419 tautomerization reaction Methods 0.000 claims description 6
- 238000007115 1,4-cycloaddition reaction Methods 0.000 claims description 5
- 230000000295 complement effect Effects 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 238000005888 cyclopropanation reaction Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000879 imine group Chemical group 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 4
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 3
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 2
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000320 amidine group Chemical group 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000003375 sulfoxide group Chemical group 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 125000005323 thioketone group Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 125000002577 pseudohalo group Chemical group 0.000 claims 1
- 125000000565 sulfonamide group Chemical group 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 13
- 239000002184 metal Substances 0.000 abstract description 13
- 238000006243 chemical reaction Methods 0.000 description 51
- 150000002431 hydrogen Chemical class 0.000 description 34
- 238000007792 addition Methods 0.000 description 26
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 125000001624 naphthyl group Chemical group 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- 239000010948 rhodium Substances 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 229910052703 rhodium Inorganic materials 0.000 description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 10
- 239000000539 dimer Substances 0.000 description 10
- 230000014509 gene expression Effects 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 229910052763 palladium Inorganic materials 0.000 description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 7
- 229910052707 ruthenium Inorganic materials 0.000 description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000000460 chlorine Chemical group 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 229910052741 iridium Inorganic materials 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 150000003003 phosphines Chemical class 0.000 description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
- 150000003573 thiols Chemical class 0.000 description 5
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 4
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 229910052762 osmium Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 150000003623 transition metal compounds Chemical class 0.000 description 4
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 125000005418 aryl aryl group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000001212 derivatisation Methods 0.000 description 3
- 150000002085 enols Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000005913 hydroamination reaction Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229960002715 nicotine Drugs 0.000 description 3
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- VNPFTLIIEKEYIW-UHFFFAOYSA-N (3-ethenylphenyl)-phenylmethanone Chemical compound C=CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 VNPFTLIIEKEYIW-UHFFFAOYSA-N 0.000 description 2
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 2
- QFGVXAGYMGCGNE-UHFFFAOYSA-N (4-ethenylphenyl)-thiophen-2-ylmethanone Chemical compound C1=CC(C=C)=CC=C1C(=O)C1=CC=CS1 QFGVXAGYMGCGNE-UHFFFAOYSA-N 0.000 description 2
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- GJYSYQQXHBPJRD-UHFFFAOYSA-N 1-(2-methylpropyl)-4-prop-1-enylbenzene Chemical compound CC=CC1=CC=C(CC(C)C)C=C1 GJYSYQQXHBPJRD-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- QDCUAHOXDLTZCU-UHFFFAOYSA-N 1-ethenyl-3-phenoxybenzene Chemical compound C=CC1=CC=CC(OC=2C=CC=CC=2)=C1 QDCUAHOXDLTZCU-UHFFFAOYSA-N 0.000 description 2
- VTMSSJKVUVVWNJ-UHFFFAOYSA-N 1-ethenyl-4-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=C(C=C)C=C1 VTMSSJKVUVVWNJ-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- GKVVFBRUOAPKMI-UHFFFAOYSA-N 2-(4-ethenylphenyl)-3h-isoindol-1-one Chemical compound C1=CC(C=C)=CC=C1N1C(=O)C2=CC=CC=C2C1 GKVVFBRUOAPKMI-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- XMRSTLBCBDIKFI-UHFFFAOYSA-N tetradeca-1,13-diene Chemical compound C=CCCCCCCCCCCC=C XMRSTLBCBDIKFI-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical class CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
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Abstract
Description
1.触媒の高い活性、2.所望のアルデヒドに関する高い選択性及び3.所望の異性体に好適な高い立体選択性。
「アキラル化合物」とは、キラルではない化合物である。
「プロキラル化合物」とは、プロキラル中心少なくとも1個を有する化合物であると理解される。「不斉合成」とは、プロキラル中心少なくとも1個を有する化合物からキラリティ中心少なくとも1個、1キラリティ軸、キラリティ面又は螺旋巻きを有する化合物を生じる反応を称しており、この際、立体異性生成物が等しくない量で生じる。
ee[%]=(R−S)/(R+S)×100にって従って得られる。R及びSは、双方のエナンチオマーのCIP−システムの記述子であり、不斉原子に付いている絶対配置を示している。エナンチオマー純粋な化合物(ee=100%)は、「ホモキラル化合物」とも称される。
A及びBは、それらの間に非共有結合性の相互作用がある相互に相補的な官能基を有する基を表し、
R1は、単結合又は二重結合した有機基を表し、
R2は、単結合した有機基を表し、
aは、プニコゲン原子の又はプソイドプニコゲン原子含有基の配位原子の価数及び基R2の結合性に依存して、0又は1であり、
この際、プニコゲン原子又はプソイドプニコゲン原子含有基の配位原子は、それらに結合している基R1、R2及びA又はBの少なくとも2個と一緒になった環系の一部分であっってもよい]。
Q1は、側面の結合の間に原子1〜5個を有する2価の架橋基を表し、
RAは、水素、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール又はヘタリールを表す、
この際、基RA、RB、RC、RDの1個又は基Q1に付いている基1個は、分子間非共有結合を形成することのできる官能基を表すか又はこのような基を含有している]の環系の一部分である。
R1=N−A又はR1=N−Bのイミン基である。この場合に好ましくは、このイミン基は、一般式I.2:
RG、RH及びRIは相互に無関係に、水素、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール又はヘタリールを表し、
この際、基RG、RH、RIの一つ又は基Q2に付いている基は、分子間非共有結合を形成することのできる官能基を表すか又はこのような基を含有している]の環系の一部分である。
RG、RH、RI及びRLは相互に無関係に、水素、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール又はヘタリールを表し、
この際、基RG、RH、RI、RK及びRLの一つは分子間非共有結合を形成することのできる官能基を表すか又はこのような基を含有している]。
I.3:
R1及びR2は相互に無関係に、アルキル、アルコキシ、シクロアルキル、シクロアルコキシ、ヘテロシクロアルキル、ヘテロシクロアルコキシ、アリール、アリールオキシ、ヘタリール又はヘタリールオキシを表すか又は
R1及びR2はそれらが結合している隣原子と一緒になって4〜8員のヘテロ環式基を表し、これは場合により付加的に1、2又は3個のシクロアルキル、ヘテロシクロアルキル、アリール又はヘタリールと融合しており、この際、ヘテロ環が存在する場合には、この融合した基は相互に無関係に、それぞれ、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール、ヘタリール、COORc、COO−M+、SO3Rc、SO3 −M+、PO3(Rc)(Rd)、(PO3)2−(M+)2、NE4E5、(NE4E5E6)+X−、ORe、SRe、(CHRfCH2O)yRe、(CH2O)yRe、(CH2CH2NE4)yRe、ハロゲン、ニトロ、アシル又はシアノから選択される置換基1、2、3又は4個を有していてよく、
ここで、Rc及びRdはそれぞれ、水素、アルキル、シクロアルキル、アリール又はヘタリールから選択される同じ又は異なる基を表し、
Re、E4、E5、E6はそれぞれ、水素、アルキル、シクロアルキル、アリール又はヘタリールから選択される同じ又は異なる基を表し、
Rfは、水素、メチル又はエチルを表し、
M+は、1カチオン当量を表し、X−は、1アニオン当量を表し、yは、1〜240の整数を表す]の基から選択されている。
Dは、それに結合している燐原子及び/又は酸素原子と一緒になって4〜8員のヘテロ環を表し、これは場合により1個、2個又は3個のシクロアルキル、ヘテロシクロアルキル、アリール及び/又はヘタリールと融合しており、この際、融合した基は相互に無関係に、それぞれアルキル、アルコキシ、ハロゲン、スルホネート、NE4E5、アルキレン−NE4E5、ニトロ、シアノ及びカルボキシレートから選択される置換基1、2、3又は4個を有していてよく、及び/又はDは、アルキル、ヒドロキシ、アルコキシ、置換又は非置換のシクロアルキル及び置換又は非置換のアリールから選択される置換基1、2、3又は4個を有していてよく、及び/又はDは、置換又は非置換のヘテロ原子1、2又は3個により中断されていてよい]。
Tは二重結合1個及び/又はアルキル−、シクロアルキル−又はアリール置換基1個を有していてよいC1〜C3−アルキレン橋を表し、この際、アリール置換基はアリールについて先に挙げられている置換基1、2又は3個を有していてよいか又は
TはO、S又はNRiにより中断されているC2〜C3−アルキレン橋を表し、
RI、RII、RIII、RIV、RV、RVI、RVII、RVIII、RIX、RX、RXI及びRXIIは相互に無関係に、水素、アルキル、シクロアルキル、アリール、アルコキシ、ハロゲン、スルホネート、NE4E5、アルキレン−NE4E5、トリフルオロメチル、ニトロ、アルコキシカルボニル又はシアノを表す]の基から選択される基を表す。
RI、RII、RIII、RIV、RV、RVI、RVII、RVIII、RIX、RX、RXI及びRXIIは相互に無関係に、水素、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール、ヘタリール、ヒドロキシ、チオール、ポリアルキレンオキシド、ポリアルキレンイミン、アルコキシ、ハロゲン、SO3H、スルホネート、NE4E5、アルキレン−NE4E5、トリフルオロメチル、ニトロ、アルコキシカルボニル、カルボキシル、アシル又はシアノを表し、ここで、E4及びE5はそれぞれ、水素、アルキル、シクロアルキル及びアリールから選択される同じ又は異なる基を表す。
R3は、水素、アルキル、アルコキシ、シクロアルキル、シクロアルコキシ、ヘテロシクロアルキル、ヘテロシクロアルコキシ、アリール、アリールオキシ、ヘタリール又はヘタリールオキシを表し、
Xは、側面の結合の間に架橋原子1〜5個を有する2価の架橋基を表し、
Yは、O、S又はNR4を表し、ここで、R4は水素、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール又はヘタリールを表し、
この際、基X及びR1〜R4の2個以上は、それらが結合している式I.a又はI.bの構造要素と一緒になって、単環−又は多環式化合物を表すことができる]の構造要素又はその互変異性体を有する。
プニコゲン−又はプソイドプニコゲン原子含有基を表わさない基R5〜R9は、相互に無関係に、水素、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール、へタリール、WCOORo、WCOO−M+、W(SO3)Ro、W(SO3)−M+、WPO3(Ro)(Rp)、W(PO3)2−(M+)2、WNE1E2、W(NE1E2E3)+X−、WORq、WSRq、(CHRrCH2O)xRq、(CH2NE1)xRq、(CH2CH2NE1)xRq、ハロゲン、ニトロ、アシル又はシアノを表し、ここで、
Wは、単結合、ヘテロ原子、ヘテロ原子含有基又は架橋原子1〜20を有する2価の架橋基を表し、
Ro及びRpはそれぞれ、アルキル、シクロアルキル、アシル又はアリールから選択される同じ又は異なる基を表し、
Rq、E1、E2、E3はそれぞれ、水素、アルキル、シクロアルキル、アシル又はアリールから選択される同じ又は異なる基を表し、
Rrは、水素、メチル又はエチルを表し、
M+は1カチオン当量を表し、X−は1アニオン当量を表し、
xは、1〜240の整数を表し、
この際、隣接基R5〜R9の2個は縮合した環系を表すこともでき、かつ
Ra及びRbは、水素、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール又はヘタリールを表し、ここで、Raはアシルを表すこともできる]の化合物及びそれらの互変異性体から選択される。
−C(=O)−Rkの基(ここで、Rkは水素、アルキル、シクロアルキル、アリール又はヘタリールを表す)から選択される。Rkは好ましくはC1〜C4−アルキル、殊にメチル、エチル、n−プロピル、イソプロピル、n−ブチル及びt−ブチルを表す。好ましいアシル基Raはピバロイル基である。
Pnは、プニコゲン−又はプソイドプニコゲン原子含有基、好ましくはN、P、As又はSb、殊にP、As又はSb、特にPを表し、
R1及びR2は、前記のように定義され、
R6〜R9は相互に無関係に、水素、C1〜C4−アルキル、C1〜C4−アルコキシ、アリール、ヘテロアリール、アシル、ハロゲン、C1〜C4−アルコキシカルボニル又はカルボキシレートを表し、
この際、隣接基R6〜R9の二つが縮合した環系を表すこともでき、かつ
Ra及びRbは、水素、アルキル、シクロアルキル又はアリールを表し、ここで、Raはアシルを表すこともできる]の化合物及びこれらの互変異性体から選択される。
6−[(R)−1,1’−ビナフチレン−2,2’−ジイルジオキシホスフィノ]−1−H−ピリジン−2−オン、6−[(S)−1,1’−ビナフチレン−2,2’−ジイルジオキシホスフィノ]−1−H−ピリジン−2−オン及び6−(3,5−ジオキサ−4−ホスファシクロヘプタ[2,1−a,3,4−a]ジナフタレン−4−イルオキシ)−1H−ピリジン−2−オン。
この際、アルキル基は、シクロアルキル、ヘテロシクロアルキル、アリール、ヘタリール、アルコキシ、シクロアルコキシ、ヘテロシクロアルコキシ、アリールオキシ、ヘタリールオキシ、ヒドロキシ、チオール、ポリアルキレンオキシド、ポリアルキレンイミン、COOH、カルボキシレート、SO3H、スルホネート、NE10E11、NE10E11E12+X−、ハロゲン、ニトロ、アシル、アシルオキシ又はシアノ(ここで、E10、E11及びE12はそれぞれ、水素、アルキル、シクロアルキル又はアリールから選択される同じ又は異なる基を表し、X−は1アニオン当量を表す)から選択される置換基1、2、3、4又は5個又はそれ以上を有していてよく、
かつこの際、シクロアルキル−、ヘテロシクロアルキル−、アリール−及びヘタリール基Rα、Rβ、Rγ及びRδは、それぞれ、アルキル及び先にアルキル基Rα及びRβ、Rγ及びRδに関して挙げられている置換基から選択される置換基1、2、3、4、5個又はそれ以上を有していてよいか、又は
基Rα、Rβ、Rγ及びRδの2個以上がそれらが結合しているC−C−二重結合と一緒になって単環−又は多環式化合物を表す。
例1:
6−(1−ナフチルフェニルホスフィノ)−2−ピバロイルアミノピリジン(6−NPPAP)の製造:
ヘテロジマーPt−錯体の製造
2−アセタミドアクリル酸メチルエステルの不斉水素化
6−DPPAPのキラルホスホナイト誘導体の製造
a)6−(ビス(ジエチルアミノ)ホスフィノ)−2−ピバロイルアミノピリジンの合成
ヘテロジマーPt−錯体の製造
Claims (28)
- それぞれプニコゲン原子含有基又はプソイドプニコゲン原子含有基1個及び分子間非共有結合を形成することのできる官能基少なくとも1個を有する配位子を有する遷移金属錯体少なくとも1種を包含するキラル触媒の存在下での、少なくとも1個のエチレン系不飽和二重結合を有するプロキラル化合物と基質との反応によって、キラル化合物を製造する方法であって、前記錯体が分子間非共有結合を介して二量化された配位子を有している方法。
- 配位子は、N、P、As及びSbから選択されているプニコゲン原子少なくとも1個を有している、請求項1に記載の方法。
- 配位子は、窒素原子少なくとも1個をイミンの形で有している、請求項2に記載の方法。
- 配位子は、プソイドプニコゲン原子としてカルベン−炭素原子少なくとも1個を有している、請求項1に記載の方法。
- 二量化された配位子のプニコゲン原子含有基又はプソイドプニコゲン原子含有基の遷移金属に配位している原子の間の間隔は最大で5Åである、請求項1から4までのいずれか1項に記載の方法。
- 分子間非共有結合を介して二量化された配位子は、式I:
A及びBは、それらの間に非共有相互作用がある、相互に相補的な官能基を有する基を表し、
R1は、単結合又は二重結合した有機基を表し、
R2は、単結合した有機基を表し、
aは、プニコゲン原子の又はプソイドプニコゲン原子含有基の配位原子の価数及び基R1の結合性に依存して0又は1であり、
この際、プニコゲン原子又はプソイドプニコゲン原子含有基の配位原子は、それに結合している基R1、R2及びA又はBの少なくとも2個と一緒になって環系の一部分であってもよい]の配位子/配位子−対から選択されている、請求項1から5までのいずれか1項に記載の方法。 - プニコゲン原子含有基又はプソイドプニコゲン原子含有基はカルベン基であり、このカルベン基は、一般式I.1:
Q1は、側面の結合の間に原子1〜5個を有する2価の架橋基を表し、
RAは、水素、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール又はヘタリールを表し、
この際、基RA、RB、RC、RDの1個又は基Q1に付いている基1個は、分子間非共有結合を形成することのできる官能基を表すか又はこのような基を含有している]の環系の一部分である、請求項1から6までのいずれか1項に記載の方法。 - プニコゲン原子含有基又はプソイドプニコゲン原子含有基は、一般式I.3:
R1及びR2は相互に無関係に、アルキル、アルコキシ、シクロアルキル、シクロアルコキシ、ヘテロシクロアルキル、ヘテロシクロアルコキシ、アリール、アリールオキシ、ヘタリール又はヘタリールオキシを表すか又は
R1及びR2はそれらが結合している隣原子と一緒になって4〜8員のヘテロ環式基を表し、これは場合により付加的に、シクロアルキル、ヘテロシクロアルキル、アリール又はヘタリール1、2又は3個と融合しており、この際、ヘテロ環及び場合により存在する融合した基は相互に無関係に、それぞれ、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール、ヘタリール、COORc、COO−M+、SO3Rc、SO3 −M+、PO3(Rc)(Rd)、(PO3)2−(M+)2、NE4E5、(NE4E5E6)+X−、ORe、SRe、(CHRfCH2O)yRe、(CH2O)yRe、(CH2CH2NE4)yRe、ハロゲン、ニトロ、アシル又はシアノから選択されている置換基1、2、3又は4個を有していてよく、
ここで、Rc及びRdはそれぞれ、水素、アルキル、シクロアルキル、アリール又はヘタリールから選択される同じ又は異なる基を表し、
Re、E4、E5、E6はそれぞれ、水素、アルキル、シクロアルキル、アリール又はヘタリールから選択される同じ又は異なる基を表し、
Rfは、水素、メチル又はエチルを表し、
M+は、1カチオン当量を表し、
X−は、1アニオン当量を表し、かつ
yは、1〜240の整数を表す]の基から選択されている、請求項1から5までのいずれか1項に記載の方法。 - 分子間非共有結合を形成することのできる官能基は、ヒドロキシル−、1級、2級及び3級アミノ−、チオール−、ケト−、チオケトン−、イミン−、カルボン酸エステル−、カルボン酸アミド−、アミジン−、ウレタン−、尿素−、スルホキシド−、スルホキシイミン−、スルホン酸アミド−及びスルホン酸エステル基から選択されている、請求項1から11までのいずれか1項に記載の方法。
- 分子間非共有結合を形成することのできる官能基は、互変異性可能である基から選択されている、請求項1から12までのいずれか1項に記載の方法。
- 配位子は、一般式I.a又はI.b:
R3は、水素、アルキル、アルコキシ、シクロアルキル、シクロアルコキシ、ヘテロシクロアルキル、ヘテロシクロアルコキシ、アリール、アリールオキシ、ヘタリール又はヘタリールオキシを表し、
Xは、側面の結合の間に架橋原子1〜5個を有する2価の架橋基を表し、
Yは、O、S又はNR4を表し、ここで、R4は水素、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール又はヘタリールを表し、
この際、基X及びR1〜R4の2個以上は、それらが結合している式I.a又はI.bの構造要素と一緒になって単環−又は多環式結合を表すことができる]の構造要素又はそれらの互変異性体少なくとも1個を包含している、請求項1から13までのいずれか1項に記載の方法。 - この際、配位子I.a又はI.b中のR1及びR2は、それらが結合している燐原子と一緒になって5−ないし8員のヘテロ環を表し、これは、場合により付加的に、シクロアルキル、ヘテロシクロアルキル、アリール又はヘタリール1、2又は3個と融合しており、この際、ヘテロ環及び場合により存在する融合した基は相互に無関係に、それぞれ、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール、ヘタリール、COORc、COO−M+、SO3Rc、SO3 −M+、PO3(Rc)(Rd)、(PO3)2−(M+)2、NE4E5、(NE4E5E6)+X−、ORe、SRe、(CHRfCH2O)yRe、(CH2NE4)yRe、(CH2CH2NE4)yRe、ハロゲン、ニトロ、アシル又はシアノから選択される置換基1、2、3又は4個を有していてよく、
ここで、Rc及びRdはそれぞれ、アルキル、シクロアルキル、アリール又はヘタリールから選択される同じ又は異なる基を表し、
Re、E4、E5、E6はそれぞれ、水素、アルキル、シクロアルキル、アシル、アリール又はヘタリールから選択される同じ又は異なる基を表し、
Rfは水素、メチル又はエチルを表し、
M+は、1カチオン当量を表し、
X−は1アニオン当量を表し、かつ
yは1〜240の整数を表す、請求項13に記載の方法。 - ヘテロ環はキラルである、請求項15に記載の方法。
- 配位子は、一般式I.A〜I.C:
プニコゲン原子含有基又はプソイドプニコゲン原子含有基を表わさない基R5〜R9は相互に無関係に、水素、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール、ヘタリール、WCOORo、WCOO−M+、W(SO3)Ro、W(SO3)−M+、WPO3(Ro)(Rp)、W(PO3)2−(M+)2、WNE1E2、W(NE1E2E3)+X−、WORq、WSRq、(CHRrCH2O)xRq、(CH2NE1)xRq、(CH2CH2NE1)xRq、ハロゲン、ニトロ、アシル又はシアノを表し、
ここで、Wは単結合、ヘテロ原子、ヘテロ原子含有基又は架橋原子1〜20個を有する2価の架橋基を表し、
Ro及びRpはそれぞれ、アルキル、シクロアルキル、アリール又はヘタリールから選択される同じ又は異なる基を表し、
Rq、E1、E2、E3はそれぞれ、水素、アルキル、シクロアルキル、アシル、アリール又はヘタリールから選択される同じ又は異なる基を表し、
Rrは、水素、メチル又はエチルを表し、
M+は1カチオン当量を表し、
X−は1アニオン当量を表し、かつ
xは1〜240の整数を表し、
ここで、隣接基R5〜R9の2個は縮合した環系を表すこともでき、かつ
Ra及びRbは、水素、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール又はヘタリールを表し、ここで、Raはアシルを表すこともできる]の化合物及びこれらの互変異性体から選択されている、請求項1から16までのいずれか1項に記載の方法。 - プニコゲン原子含有基又はプソイドプニコゲン原子含有基を表す基R5〜R9は、式:−W’−PnR1R2
[式中、Pnは、プニコゲン原子又はプソイドプニコゲン原子を表し、W’は、単結合、ヘテロ原子、ヘテロ原子含有基又は側面の結合の間に架橋原子1〜4個を有する2価の架橋基を表し、R1及びR2は請求項13又は14に定義されているものを表す]の基を表す、請求項17に記載の方法。 - 一般式I.A〜I.C:
プニコゲン原子含有基又はプソイドプニコゲン原子含有基を表さない基R5〜R9は相互に無関係に、水素、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール、ヘタリール、WCOORo、WCOO−M+、W(SO3)Ro、W(SO3)−M+、WPO3(Ro)(Rp)、W(PO3)2−(M+)2、WNE1E2、W(NE1E2E3)+X−、WORq、WSRq、(CHRrCH2O)xRq、(CH2NE1)xRq、(CH2CH2NE1)xRq、ハロゲン、ニトロ、アシル又はシアノを表し、
ここで、Wは単結合、ヘテロ原子、ヘテロ原子含有基又は架橋原子1〜20個を有する2価の架橋基を表し、
Ro及びRpはそれぞれ、アルキル、シクロアルキル、アリール又はヘタリールから選択される同じ又は異なる基を表し、
Rq、E1、E2、E3はそれぞれ、水素、アルキル、シクロアルキル、アシル、アリール又はヘタリールから選択される同じ又は異なる基を表し、
Rrは水素、メチル又はエチルを表し、
M+は1カチオン当量を表し、
X−は1アニオン当量を表し、かつ
xは1〜240の整数を表し、
ここで、隣接している基R5〜R9の2個は縮合環系を表すこともでき、かつ、
Ra及びRbは、水素、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール又はヘタリールを表し、ここで、Raはアシルを表すこともできる]の化合物及びこれらの互変異性体から選択されている配位子を有する遷移金属錯体少なくとも1種を包含するキラル触媒の存在下での、少なくとも1個のエチレン系不飽和二重結合を有するプロキラル化合物と基質との反応によって、キラル化合物を製造する方法。 - 配位子は、一般式I.i〜I.iii:
Pnはプニコゲン原子含有基又はプソイドプニコゲン原子含有基を表し、
R1及びR2は請求項13又は14に定義されているものを表し、
R6〜R9は相互に無関係に、水素、C1〜C4−アルキル、C1〜C4−アルコキシ、アリール、ヘテロアリール、アシル、ハロゲン、C1〜C4−アルコキシカルボニル又はカルボキシレートを表し、
ここで、隣接基R6〜R9の2個は縮合環系を表すこともでき、かつ、
Ra及びRbは水素、アルキル、シクロアルキル又はアリールを表し、ここで、Raはアシルを表すこともできる]の化合物及びこれらの互変異性体から選択されている、請求項17から19までのいずれか1項に記載の方法。 - プロキラル化合物は、オレフィン、アルデヒド、ケトン及びイミンから選択されている、請求項1から20までのいずれか1項に記載の方法。
- 水素化、ヒドロホルミル化、ヒドロシアン化、カルボニル化、ヒドロアシル化、ヒドロアミド化、ヒドロエステル化、ヒドロシリル化、ヒドロホウ素化、アミノ分解、アルコール分解、異性化、メタセシス、シクロプロパン化、アルドール縮合、アリルアルキル化又は[4+2]−シクロ付加である、請求項1から21までのいずれか1項に記載の方法。
- 1,2−付加、有利には1−ヒドロ−2−カルボ−付加である、請求項1から22までのいずれか1項に記載の方法。
- ヒドロホルミル化である、請求項1から23までのいずれか1項に記載の方法。
- 水素化である、請求項1から24までのいずれか1項に記載の方法。
- 請求項1から20までのいずれか1項に定義されているような配位子。
- 請求項1から20までのいずれか1項に定義されているような触媒。
- 水素化、ヒドロホルミル化、ヒドロシアン化、カルボニル化、ヒドロアシル化、ヒドロアミド化、ヒドロエステル化、ヒドロシリル化、ヒドロホウ素化、アミノ分解、アルコール分解、異性化、メタセシス、シクロプロパン化、アルドール縮合、アリルアルキル化又は[4+2]−シクロ付加のための、請求項27に記載の触媒の使用。
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