JP4948172B2 - 触媒を用いたプロキラル環状無水物およびメソ環状無水物の不斉脱対称化 - Google Patents
触媒を用いたプロキラル環状無水物およびメソ環状無水物の不斉脱対称化 Download PDFInfo
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- JP4948172B2 JP4948172B2 JP2006529361A JP2006529361A JP4948172B2 JP 4948172 B2 JP4948172 B2 JP 4948172B2 JP 2006529361 A JP2006529361 A JP 2006529361A JP 2006529361 A JP2006529361 A JP 2006529361A JP 4948172 B2 JP4948172 B2 JP 4948172B2
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- Prior art keywords
- catalyst
- alkenyl
- anhydride
- alkyl
- certain embodiments
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- -1 cyclic anhydrides Chemical class 0.000 title claims description 185
- 125000004122 cyclic group Chemical group 0.000 title claims description 13
- 230000003197 catalytic effect Effects 0.000 title description 36
- 238000010596 desymmetrization reaction Methods 0.000 title description 28
- 238000000034 method Methods 0.000 claims description 244
- 239000003054 catalyst Substances 0.000 claims description 187
- 238000006243 chemical reaction Methods 0.000 claims description 159
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 126
- 150000001875 compounds Chemical class 0.000 claims description 87
- 239000012038 nucleophile Substances 0.000 claims description 85
- 125000003342 alkenyl group Chemical group 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 51
- 150000008064 anhydrides Chemical class 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 230000008569 process Effects 0.000 claims description 27
- 125000000304 alkynyl group Chemical group 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 135
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 121
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 101
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 73
- 239000000203 mixture Substances 0.000 description 61
- 239000000047 product Substances 0.000 description 58
- 239000000758 substrate Substances 0.000 description 58
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 37
- 239000000243 solution Substances 0.000 description 37
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- 239000010410 layer Substances 0.000 description 34
- 239000011734 sodium Substances 0.000 description 33
- 239000012044 organic layer Substances 0.000 description 32
- 239000002904 solvent Substances 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
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- 238000006136 alcoholysis reaction Methods 0.000 description 27
- 238000002474 experimental method Methods 0.000 description 27
- 239000007858 starting material Substances 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- 241000157855 Cinchona Species 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical class O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 23
- 238000006140 methanolysis reaction Methods 0.000 description 23
- 150000001412 amines Chemical class 0.000 description 22
- 230000002829 reductive effect Effects 0.000 description 22
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 20
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- 230000000694 effects Effects 0.000 description 20
- 229940014800 succinic anhydride Drugs 0.000 description 20
- 229920006395 saturated elastomer Polymers 0.000 description 19
- 125000001424 substituent group Chemical group 0.000 description 19
- 229930013930 alkaloid Natural products 0.000 description 18
- 125000004429 atom Chemical group 0.000 description 17
- 239000002585 base Substances 0.000 description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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- 239000000376 reactant Substances 0.000 description 16
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 150000001408 amides Chemical class 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 150000002576 ketones Chemical group 0.000 description 15
- 150000003573 thiols Chemical class 0.000 description 15
- 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 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
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- 150000003797 alkaloid derivatives Chemical class 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 14
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- 238000004458 analytical method Methods 0.000 description 13
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- 238000002360 preparation method Methods 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- 229910000104 sodium hydride Inorganic materials 0.000 description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 239000002480 mineral oil Substances 0.000 description 12
- 235000010446 mineral oil Nutrition 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 125000000623 heterocyclic group Chemical group 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 150000002466 imines Chemical class 0.000 description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 11
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 11
- 150000003138 primary alcohols Chemical class 0.000 description 11
- 150000003346 selenoethers Chemical class 0.000 description 11
- 150000003512 tertiary amines Chemical class 0.000 description 11
- 150000003568 thioethers Chemical class 0.000 description 11
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- HXFIRQHMXJBTRV-UHFFFAOYSA-N 3,4-dimethyloxolane-2,5-dione Chemical compound CC1C(C)C(=O)OC1=O HXFIRQHMXJBTRV-UHFFFAOYSA-N 0.000 description 10
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 10
- 238000005356 chiral GC Methods 0.000 description 10
- 0 COc1cc2c([C@@](C3N(CC4)CC(*)C4C3)O)ccnc2cc1 Chemical compound COc1cc2c([C@@](C3N(CC4)CC(*)C4C3)O)ccnc2cc1 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- MGICRVTUCPFQQZ-UHFFFAOYSA-N 4-methyloxane-2,6-dione Chemical compound CC1CC(=O)OC(=O)C1 MGICRVTUCPFQQZ-UHFFFAOYSA-N 0.000 description 8
- 125000002252 acyl group Chemical group 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 125000004404 heteroalkyl group Chemical group 0.000 description 8
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 8
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 8
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 125000000547 substituted alkyl group Chemical group 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
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- 125000005842 heteroatom Chemical group 0.000 description 7
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
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- RTCUCQWIICFPOD-SECBINFHSA-N (1r)-1-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C([C@H](N)C)=CC=CC2=C1 RTCUCQWIICFPOD-SECBINFHSA-N 0.000 description 6
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XHQPKRVACXDVNV-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) 2-chloroacetate Chemical compound CC(C)C1CCC(C)CC1OC(=O)CCl XHQPKRVACXDVNV-UHFFFAOYSA-N 0.000 description 5
- TWOVHUYOMTVDRB-BDCWUMDOSA-N 4-[(r)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-phenanthren-9-yloxymethyl]-6-methoxyquinoline Chemical compound C1=C(OC)C=C2C([C@@H](OC=3C4=CC=CC=C4C4=CC=CC=C4C=3)[C@@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 TWOVHUYOMTVDRB-BDCWUMDOSA-N 0.000 description 5
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- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
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- 150000002738 metalloids Chemical class 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- AIIAHNREQDTRFI-UHFFFAOYSA-N oxiran-2-ylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1CO1 AIIAHNREQDTRFI-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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- 238000007086 side reaction Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical group C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Catalysts (AREA)
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
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US47753103P | 2003-06-11 | 2003-06-11 | |
US60/477,531 | 2003-06-11 | ||
US10/460,051 US7053236B2 (en) | 2000-04-04 | 2003-06-12 | Catalytic asymmetric desymmetrization of prochiral and meso compounds |
US10/460,051 | 2003-06-12 | ||
US48421803P | 2003-07-01 | 2003-07-01 | |
US60/484,218 | 2003-07-01 | ||
PCT/US2004/018690 WO2004110609A2 (en) | 2003-06-11 | 2004-06-11 | Catalytic asymmetric desymmetrization of prochiral and meso cyclic anhydrides |
Publications (3)
Publication Number | Publication Date |
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JP2007531704A JP2007531704A (ja) | 2007-11-08 |
JP2007531704A5 JP2007531704A5 (zh) | 2011-06-16 |
JP4948172B2 true JP4948172B2 (ja) | 2012-06-06 |
Family
ID=33556345
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JP2006529361A Expired - Fee Related JP4948172B2 (ja) | 2003-06-11 | 2004-06-11 | 触媒を用いたプロキラル環状無水物およびメソ環状無水物の不斉脱対称化 |
Country Status (7)
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EP (1) | EP1638677A4 (zh) |
JP (1) | JP4948172B2 (zh) |
KR (1) | KR20060070485A (zh) |
CN (1) | CN1956943A (zh) |
CA (1) | CA2529071A1 (zh) |
HR (1) | HRP20060010A2 (zh) |
WO (1) | WO2004110609A2 (zh) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101157655A (zh) * | 2007-09-20 | 2008-04-09 | 复旦大学 | (4s,5r)-半酯的合成方法 |
CN101284837B (zh) * | 2008-06-05 | 2011-07-20 | 复旦大学 | (+)-生物素立体选择性全合成方法 |
WO2010094210A1 (zh) * | 2009-02-18 | 2010-08-26 | 帝斯曼知识产权资产管理有限公司 | (4s,5r)-半酯的制备方法 |
CN102686558A (zh) | 2009-12-25 | 2012-09-19 | 株式会社钟化 | 光学活性3-取代戊二酸单酰胺的制造方法 |
JP5879228B2 (ja) * | 2012-08-13 | 2016-03-08 | 大阪有機化学工業株式会社 | アダマンタン誘導体 |
JP6090621B2 (ja) * | 2012-12-05 | 2017-03-08 | 三菱レイヨン株式会社 | 重合性単量体の製造方法 |
CN105566248B (zh) * | 2015-12-30 | 2019-03-26 | 苏州开元民生科技股份有限公司 | 地尔硫卓手性中间体的选择性合成方法 |
CN110754474B (zh) * | 2019-10-21 | 2021-10-26 | 河南科技大学 | 奎尼定或奎尼定类衍生物的应用、植物源杀虫剂、奎尼定类衍生物及其制备方法 |
CN116217319A (zh) * | 2023-03-02 | 2023-06-06 | 哈尔滨工业大学(深圳) | 一种内消旋烯丙基醚的去对称化反应的方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US5260461A (en) * | 1988-01-11 | 1993-11-09 | Massachusetts Institute Of Technology | Ligands for ADH: cinchona alkaloids and moderately sized organic substituents linked through a planar aromatic spacer group |
US6580003B2 (en) * | 2000-04-04 | 2003-06-17 | Brandeis University | Catalytic asymmetric desymmetrization of meso compounds |
US7053236B2 (en) * | 2000-04-04 | 2006-05-30 | Brandeis University | Catalytic asymmetric desymmetrization of prochiral and meso compounds |
TWI298067B (en) * | 2002-01-31 | 2008-06-21 | Daiso Co Ltd | New optically active compound, method for kinetic resolution of carbonic acid derivatives and catalyst thereof |
-
2004
- 2004-06-11 WO PCT/US2004/018690 patent/WO2004110609A2/en active Application Filing
- 2004-06-11 KR KR1020057023832A patent/KR20060070485A/ko not_active Application Discontinuation
- 2004-06-11 CN CNA2004800228879A patent/CN1956943A/zh active Pending
- 2004-06-11 CA CA002529071A patent/CA2529071A1/en not_active Abandoned
- 2004-06-11 EP EP04755066A patent/EP1638677A4/en not_active Withdrawn
- 2004-06-11 JP JP2006529361A patent/JP4948172B2/ja not_active Expired - Fee Related
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2006
- 2006-01-10 HR HR20060010A patent/HRP20060010A2/hr not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
EP1638677A2 (en) | 2006-03-29 |
CA2529071A1 (en) | 2004-12-23 |
JP2007531704A (ja) | 2007-11-08 |
EP1638677A4 (en) | 2007-10-10 |
HRP20060010A2 (en) | 2006-06-30 |
KR20060070485A (ko) | 2006-06-23 |
CN1956943A (zh) | 2007-05-02 |
WO2004110609A2 (en) | 2004-12-23 |
WO2004110609A3 (en) | 2007-01-04 |
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