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

外国特許コード F110003809
整理番号 E07608US1
掲載日 2011年7月5日
出願国 アメリカ合衆国
出願番号 56793609
公報番号 20100029968
公報番号 7910762
出願日 平成21年9月28日(2009.9.28)
公報発行日 平成22年2月4日(2010.2.4)
公報発行日 平成23年3月22日(2011.3.22)
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
  • 2007US-11589259 (2007.5.23) US
発明の名称 (英語) Asymmetric reaction catalyst and method for preparing optically active compound using the same
発明の概要(英語) (US7910762)
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 tetraol 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 tetraol is represented by the following formula (III):

wherein R3 represents a hydrogen atom, a halogen atom, a perfluoroalkyl group having at most 4 carbons, or an alkyl group or alkoxy group having at most 4 carbons and R4 represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbons.
[claim4]
4. An asymmetric reaction catalyst according to claim 2, wherein the tetraol is represented by the following formula (III):

wherein R3 represents a hydrogen atom, a halogen atom, a perfluoroalkyl group having at most 4 carbons, or an alkyl group or alkoxy group having at most 4 carbons and R4 represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbons.
[claim5]
5. 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 1.
[claim6]
6. A method for preparing an optically active compound according to claim 5, wherein the above-mentioned reaction substrate is an imine represented by the following formula (IV):

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 R9 represents a hydrogen atom or a trifluoromethyl group.
[claim7]
7. A method for preparing an optically active compound according to claim 5, wherein the above-mentioned nucleophilic agent is a silicon enolate represented by the following formula (VI):

wherein R10 and R11 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; R12 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 R13, being the same or different, represents a hydrocarbon group.
[claim8]
8. A method for preparing an optically active compound according to claim 5, wherein an imidazole derivative is added to the reaction system.
[claim9]
9. 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.
[claim10]
10. A method for preparing an optically active compound according to claim 9, wherein the reaction substrate is an epoxide, the nucleophilic agent is a nitrogen compound, and the optically active compound is a nitrogen-containing compound.
  • 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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