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Process for the production of optically active hydroxymethylated compounds

外国特許コード F110003942
整理番号 E07601WO
掲載日 2011年7月7日
出願国 欧州特許庁(EPO)
出願番号 05704190
公報番号 1724251
公報番号 1724251
出願日 平成17年1月27日(2005.1.27)
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9月16日(2015.9.16)
国際出願番号 JP2005001086
国際公開番号 WO2005073156
国際出願日 平成17年1月27日(2005.1.27)
国際公開日 平成17年8月11日(2005.8.11)
優先権データ
  • 2005JP001086 (2005.1.27) WO
  • 特願2004-023338 (2004.1.30) JP
発明の名称 (英語) Process for the production of optically active hydroxymethylated compounds
発明の概要(英語) The present invention presents a catalyst that allows asymmetric hydroxymethylation reactions to progress with excellent asymmetric selectivity and a production method for optically active hydroxymethylated compounds using the catalyst.
Optically active hydroxymethylated compounds are obtained with excellent asymmetric selectivity by using a catalyst obtained by mixing chiral ligands (for example, chemical formula 4) with scandium triflate and the like.
特許請求の範囲(英語) [claim1]
1. A method for producing an optically active hydroxymethylated compound, comprising reacting a silicon enolate and formaldehyde, in the presence of a catalyst, in an aqueous solution or a mixed solvent of water and an organic solvent,
wherein the silicon enolate is represented by the following formula (chemical formula 2): (see diagramm) wherein R **5 is a hydrogen atom or an alkyl group, R **6 is an alkyl group, an alkyl aryl group or an aryl group, in which R **6 and R **6 may together form a five to six membered ring comprising carbon atoms and optional hetero atoms, R **7 is a hydrogen atom, an alkyl group, an alkyl aryl group or an aryl group and the groups R **8, which may be identical or different, are each alkyl group, and the catalyst is obtained by mixing a ligand or its symmetric isomer and a Lewis acid, wherein the ligand is represented by the following formula (chemical formula 1): (see diagramm) wherein R **1 and R **2, may be identical or different, are hydrogen atoms, alkyl groups or aryl groups, at least one of R **1 and R **2 contains at least three carbon atoms, R **3 and R **4, may be identical or different, are hydrogen atoms, alkyl groups containing one to four carbon atoms or alkoxy groups, X **1 and X **2, may be identical or different, are represented by -OH, -SH or -NHR **11, wherein R **11 is a hydrogen atom or an alkyl group, and the Lewis acid is represented by MYn, wherein M is Cu, Zn, Fe, Sc or a lanthanoid element, Y is a halogen atom, OAc, OCOCF 3, ClO 4, SbF 6, PF 6 or OSO 2CF 3 and n is 2 or 3.
[claim2]
2. A catalyst obtained by mixing a ligand or its symmetric isomer and a Lewis acid, wherein the ligand is represented by the following formula (chemical formula 1): (see diagramm) wherein R **1 and R **2, may be identical or different, are hydrogen atoms, alkyl groups or aryl groups, at least one of R **1 and R **2 contains at least three carbon atoms, R **3 and R **4, may be identical or different, are hydrogen atoms, alkyl groups containing one to four carbon atoms or alkoxy groups, X **1 and X **2, may be identical or different, are represented by -OH, -SH or -NHR **11, wherein R **11 is a hydrogen atom or an alkyl group, and the Lewis acid is represented by MY n, wherein M is Fe, Sc or a lanthanoid element, Y is a halogen atom, OAc, OCOCF 3, ClO 4, SbF 6, PF 6 or OSO 2CF 3 and n is 2 or 3.
  • 出願人(英語)
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • 発明者(英語)
  • KOBAYASHI SHU
  • MANABE KEI
国際特許分類(IPC)
欧州特許分類/主・副
  • M07C101/08
  • M07C101/14
  • M07C101/18
  • M07C102/08
  • M07C102/10
指定国 Contracting States: CH DE FR GB LI
参考情報 (研究プロジェクト等) ERATO KOBAYASHI Highly Functionalized Reaction Environments AREA
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