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

外国特許コード F110003948
整理番号 E07608WO
掲載日 2011年7月7日
出願国 欧州特許庁(EPO)
出願番号 05720349
公報番号 1724013
公報番号 1724013
出願日 平成17年3月9日(2005.3.9)
公報発行日 平成18年11月22日(2006.11.22)
公報発行日 平成27年1月28日(2015.1.28)
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
  • 2005JP004077 (2005.3.9) WO
  • 特願2004-064994 (2004.3.9) JP
発明の名称 (英語) Asymmetric reaction catalyst and process for production of optically active compounds with the same
発明の概要(英語) 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).
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 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.
  • 出願人(英語)
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • 発明者(英語)
  • KOBAYASHI SHU
  • ISHITANI HARURO
  • YAMASHITA YASUHIRO
国際特許分類(IPC)
欧州特許分類/主・副
  • C07D333/24
  • C07D307/54
  • C07C327/22
  • C07C221/00
  • C07B053/00
  • B01J031/22B2H2
指定国 Contracting States: DE FR GB
参考情報 (研究プロジェクト等) ERATO KOBAYASHI Highly Functionalized Reaction Environments AREA
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