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Asymmetric reaction catalyst and method for preparing optically active compound using the same

Foreign code F110003810
File No. E07608WO
Posted date Jul 5, 2011
Country United States of America
Application number 58925905
Gazette No. 20070265472
Gazette No. 7667078
Date of filing Mar 9, 2005
Gazette Date Nov 15, 2007
Gazette Date Feb 23, 2010
International application number JP2005004077
International publication number WO2005084803
Date of international filing Mar 9, 2005
Date of international publication Sep 15, 2005
Priority data
  • P2004-064994 (Mar 9, 2004) JP
  • 2005WO-JP04077 (Mar 9, 2005) WO
Title Asymmetric reaction catalyst and method for preparing optically active compound using the same
Abstract (US7667078)
An asymmetric reaction catalyst is obtained by mixing a pentavalent niobium compound and an optically active triol or tetraol having a binaphthol structure of R or S configuration, and the triol is represented by the following formula: (wherein, Y is divalent hydrocarbon and R1 is a hydrogen atom, a halogen atom, a trifluoromethyl group, or an alkyl group or alkoxy group having at most 4 carbons).
Scope of claims [claim1]
1. An asymmetric reaction catalyst obtained by mixing a pentavalent niobium compound and a triol having an optically active binapthol structure of R or S configuration, wherein the asymmetric reaction catalyst can catalyze an asymmetric reaction selected from the group consisting of an asymmetric Mannich reaction, an epoxide asymmetric ring opening reaction, an asymmetric allylation reaction, an asymmetric cyanation reaction and an asymmetric alkylation reaction.
[claim2]
2. An asymmetric reaction catalyst according to claim 1, wherein the niobium compound is represented by the following formula:
NbX5
(wherein, X is an alkoxide or a halogen atom).
[claim3]
3. An asymmetric reaction catalyst according to claim 1, wherein the triol is represented by the following formula (I):

wherein Y represents a divalent hydrocarbon group and R1 represents a hydrogen atom, a halogen atom, a perfluoroalkyl group having at most four carbons, or an alkyl group or alkoxy group having at most 4 carbons.
[claim4]
4. An asymmetric reaction catalyst according to claim 2, wherein the triol is represented by the following formula (I):

wherein Y represents a divalent hydrocarbon group and R1 represents a hydrogen atom, a halogen atom, a perfluoroalkyl group having at most four carbons, or an alkyl group or alkoxy group having at most 4 carbons.
[claim5]
5. An asymmetric reaction catalyst according to claim 1, wherein the triol is represented by the following formula (II):

wherein R1 represents a hydrogen atom, a halogen atom, a perfluoroalkyl group having at most 4 carbons, or an alkyl group or an alkoxy group having at most four carbons; R2 represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbons; and n is an integer from 0 to 2.
[claim6]
6. An asymmetric reaction catalyst according to claim 2, wherein the triol is represented by the following formula (II):
wherein R1 represents a hydrogen atom, a halogen atom, a perfluoroalkyl group having at most 4 carbons, or an alkyl group or an alkoxy group having at most four carbons; R2 represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbons; and n is an integer from 0 to 2.
[claim7]
7. A method for preparing an optically active compound, wherein a reaction substrate represented by R5R6C.dbd.N-Z (wherein R5 and R6, not being the same, are selected from the group consisting of a hydrogen atom, a hydrocarbon group, an aikoxycarbonyl group, and a hydrocarbon group having a functional group and Z represents an aryl group or an acylamino group) and a nucleophilic agent are reacted by nucleophilic addition using an asymmetric reaction catalyst according to claim 1.
[claim8]
8. A method for preparing an optically active compound, wherein a reaction substrate represented by R5R6C.dbd.N-Z (wherein R5 and R6, not being the same, are selected from the group consisting of a hydrogen atom, a hydrocarbon group, an alkoxycarbonyl group, and a hydrocarbon group having a functional group and Z represents an aryl group or an acylamino group) and a nucleophilic agent are reacted by nucleophilic addition using an asymmetric reaction catalyst according to claim 2.
[claim9]
9. A method for preparing an optically active compound, wherein a reaction substrate represented by R5R6C.dbd.N-Z (wherein R5 and R6, not being the same, are selected from the group consisting of a hydrogen atom, a hydrocarbon group, an alkoxycarbonyl group, and a hydrocarbon group having a functional group and Z represents an awl group or an acylamino group) and a nucleophilic agent are reacted by nucleophilic addition using an asymmetric reaction catalyst according to claim 3.
[claim10]
10. A method for preparing an optically active compound, wherein a reaction substrate represented by R5R6C.dbd.N-Z (wherein R5 and R6, not being the same, are selected from the group consisting of a hydrogen atom, a hydrocarbon group, an alkoxycarbonyl group, and a hydrocarbon group having a functional group and Z represents an aryl group or an acylamino group) and a nucleophilic agent are reacted by nucleophilic addition using an asymmetric reaction catalyst according to claim 4.
[claim11]
11. A method for preparing an optically active compound, wherein a reaction substrate represented by R5R6C.dbd.N-Z (wherein R5 and R6, not being the same, are selected from the group consisting of a hydrogen atom, a hydrocarbon group, an alkoxycarbonyl group, and a hydrocarbon group having a functional group and Z represents an aryl group or an acylamino group) and a nucleophilic agent are reacted by nucleophilic addition using an asymmetric reaction catalyst according to claim 5.
[claim12]
12. A method for preparing an optically active compound according to claim 7, wherein the above-mentioned reaction substrate is a benzoylhydrazone represented by the following formula (V):

wherein R7 and R8, not being the same, are selected from the group consisting of a hydrogen atom, a hydrocarbon group, and a hydrocarbon group having a functional group and R14 represents a hydrogen atom or a substituent having an electron-withdrawing property.
[claim13]
13. A method for preparing an optically active compound according to claim 7, wherein a synthetic crystalline zeolite is added to the reaction system.
[claim14]
14. A method for preparing a optically active compound wherein a reaction substrate and a nucleophilic agent are reacted by nucleophilic addition using an asymmetric reaction catalyst according to claim 1.
  • Inventor, and Inventor/Applicant
  • KOBAYASHI SHU
  • ISHITANI HARURO
  • YAMASHITA YASUHIRO
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
IPC(International Patent Classification)
Reference ( R and D project ) ERATO KOBAYASHI Highly Functionalized Reaction Environments AREA
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