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

外国特許コード F110003810
整理番号 E07608WO
掲載日 2011年7月5日
出願国 アメリカ合衆国
出願番号 58925905
公報番号 20070265472
公報番号 7667078
出願日 平成17年3月9日(2005.3.9)
公報発行日 平成19年11月15日(2007.11.15)
公報発行日 平成22年2月23日(2010.2.23)
国際出願番号 JP2005004077
国際公開番号 WO2005084803
国際出願日 平成17年3月9日(2005.3.9)
国際公開日 平成17年9月15日(2005.9.15)
優先権データ
  • 特願2004-064994 (2004.3.9) JP
  • 2005WO-JP04077 (2005.3.9) WO
発明の名称 (英語) Asymmetric reaction catalyst and method for preparing optically active compound using the same UPDATE
発明の概要(英語) (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).
特許請求の範囲(英語) [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.
  • 発明者/出願人(英語)
  • KOBAYASHI SHU
  • ISHITANI HARURO
  • YAMASHITA YASUHIRO
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
参考情報 (研究プロジェクト等) ERATO KOBAYASHI Highly Functionalized Reaction Environments AREA
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