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Method of enantioselective nucleophilic addition reaction of enamide to imine and synthesis method of alpha -amino-gamma -keto acid ester

外国特許コード F110005247
整理番号 B14-03WO
掲載日 2011年8月29日
出願国 アメリカ合衆国
出願番号 58707505
公報番号 20070161804
公報番号 7754898
出願日 平成17年1月24日(2005.1.24)
公報発行日 平成19年7月12日(2007.7.12)
公報発行日 平成22年7月13日(2010.7.13)
国際出願番号 JP2005001282
国際公開番号 WO2005070876
国際出願日 平成17年1月24日(2005.1.24)
国際公開日 平成17年8月4日(2005.8.4)
優先権データ
  • 特願2004-016407 (2004.1.23) JP
  • 2005WO-JP01282 (2005.1.24) WO
発明の名称 (英語) Method of enantioselective nucleophilic addition reaction of enamide to imine and synthesis method of alpha -amino-gamma -keto acid ester
発明の概要(英語) (US7754898)
An asymmetric synthesis of amino acid compound that is useful as a starting material or synthetic intermediate for production of medicinal products, agrichemicals, perfumes, functional polymers, etc.
There is provided a method of enanthio-selective nucleophilic addition reaction to imine compound being a method of nucleophilic addition reaction of enamide compound accompanied by amino formation to imino group (—CH═N—) of imine compound, characterized in that the reaction is performed in the presence of a chiral copper catalyst.
Further, there is provided a novel method of synthesizing an amino acid compound, etc., to which the above is applied.
特許請求の範囲(英語) [claim1]
1. A method of an enantioselective nucleophilic addition reaction of enamide, which comprises reacting an enamide compound and an imine compound in the presence of a chiral copper catalyst to produce a compound with an amino group formed from an imino group ( -- CH.dbd.N -- ) of the imine compound generated by the nucleophilic addition reaction, the chiral copper catalyst being a bivalent copper compound which is a salt of an organic or inorganic acid or a complex or composite of the salt, and a chiral diamine ligand selected from the group consisting of the compounds represented by the following formulae:

where R represents a hydrocarbon group which may have a substituent.
[claim2]
2. A method for synthesizing an optically active alpha -amino-gamma -imino acid ester, which is the method of the enantioselective nucleophilic addition reaction of enamide according to claim 1, wherein the imine compound is represented by the following formula (1):
(wherein R1 represents a hydrocarbon group which may have a substituent; R2 represents an R0 -- CO -- or R0 -- O -- CO -- group, wherein R0 represents a hydrocarbon group which may have a substituent); and the enamide compound is represented by the following formula (2):
(wherein R3 represents a hydrocarbon group which may have a substituent or a hydrocarbon group which may have a substituent to be bonded via an oxygen atom; R4 represents a hydrocarbon group which may have a substituent; and R5 and R6 may be same or different from each other and each represents a hydrogen atom or a hydrocarbon group which may have a substituent, wherein at least one of them represents a hydrogen atom), and generates a compound represented by at least one of the following formulae (3):
(wherein R1, R2, R3, R4, R5 and R6 are defined above).
[claim3]
3. A method for synthesizing an optically active alpha -amino-gamma -keto acid ester, which comprises, after the nucleophilic addition reaction according to claim 2, performing an acid treatment to thereby generate a compound represented by at least one of the following formulae (4):
(wherein R1, R2, R4, R5 and R6 are defined above).
[claim4]
4. A method for synthesizing an optically active alpha , gamma -diamino acid ester, which comprises, after the nucleophilic addition reaction according to claim 2, performing a reduction treatment to thereby generate a compound represented by at least one of the following formulae (5):
(wherein R1, R2, R3, R4, R5 and R6 are defined above).
[claim5]
5. A method for synthesizing optically active gamma -lactams, which comprises removing an acyl group of a gamma -amino group of the optically active alpha , gamma -diamino acid ester synthesized by the method according to claim 4, to thereby generate a compound represented by at least one of the following formulae (6):
(wherein R2, R4, R5 and R6 are defined above).
  • 発明者/出願人(英語)
  • KOBAYASHI SHU
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
米国特許分類/主・副
  • 548/550
  • 560/169
  • 564/152
参考情報 (研究プロジェクト等) SORST Selected in Fiscal 2001
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