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Asymmetric reaction catalyst and process for production of optically active compounds with the same

Foreign code F110003948
File No. E07608WO
Posted date Jul 7, 2011
Country EPO
Application number 05720349
Gazette No. 1724013
Gazette No. 1724013
Date of filing Mar 9, 2005
Gazette Date Nov 22, 2006
Gazette Date Jan 28, 2015
International application number JP2005004077
International publication number WO2005084803
Date of international filing Mar 9, 2005
Date of international publication Sep 15, 2005
Priority data
  • 2005JP004077 (Mar 9, 2005) WO
  • P2004-064994 (Mar 9, 2004) JP
Title Asymmetric reaction catalyst and process for production of optically active compounds with the same
Abstract 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: (see diagramm) (wherein, Y is divalent hydrocarbon and R **1 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 binaphtol structure of R or S configuration, wherein the triol is represented by the following formula (II): (see diagramm) wherein, R **1 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; R **2 represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbons; and n is an integer from 0 to 2.
[claim2]
2. An asymmetric reaction catalyst according to claim 1, wherein the niobium compound is represented by the following formula:

NbX 5

wherein, X is an alkoxide or a halogen atom.
[claim3]
3. A method for preparing an optically active compound, wherein a reaction substrate represented by R **5R **6C=N-Z wherein R **5 and R **6, 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 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 any one of claims 1 or 2.
[claim4]
4. A method for preparing an optically active compound according to claim 3, wherein the above-mentioned reaction substrate is an imine represented by the following formula (IV) : (see diagramm) wherein, R **7 and R **8, 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 R **9 represents a hydrogen atom or a trifluoromethyl group.
[claim5]
5. A method for preparing an optically active compound according to claim 3, wherein the above-mentioned reaction substrate is a benzoylhydrazone represented by the following formula (V): (see diagramm) wherein, R **7 and R **8, 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 R **14 represents a hydrogen atom or a substituent having an electron-withdrawing property.
[claim6]
6. A method for preparing an optically active compound according to any one of claims 3 to 5, wherein the above-mentioned nucleophilic agent is a silicon enolate represented by the following formula (VI): (see diagramm) wherein R **10 and R **11 are each independently one selected from the group consisting of a hydrogen atom, an aliphatic hydrocarbon group, an aromatic hydrocarbon group, an alkyloxy group, an aryloxy group, and an silyloxy group; R **12 is one selected from the group consisting of a hydrogen atom, an aliphatic hydrocarbon group, an alkyloxy group, an aryloxy group, an arylthio group, and a alkylthio group; and each R **13, being the same or different, represents a hydrocarbon group.
[claim7]
7. A method for preparing an optically active compound according to any one of claims 3 to 6, wherein an imidazole derivative is added to the reaction system.
[claim8]
8. A method for preparing an optically active compound system according to any one of claims 3 to 7, wherein a synthetic crystalline zeolite is added to the reaction system.
  • Applicant
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • Inventor
  • KOBAYASHI SHU
  • ISHITANI HARURO
  • YAMASHITA YASUHIRO
IPC(International Patent Classification)
Reference ( R and D project ) ERATO KOBAYASHI Highly Functionalized Reaction Environments AREA
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