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Process for asymmetric intramolecular (3+2) cyclo-addition of hydrazones

外国特許コード F110003292
整理番号 A051-88EP
掲載日 2011年6月22日
出願国 欧州特許庁(EPO)
出願番号 03710300
公報番号 1489072
公報番号 1489072
出願日 平成15年3月11日(2003.3.11)
公報発行日 平成16年12月22日(2004.12.22)
公報発行日 平成28年1月20日(2016.1.20)
国際出願番号 JP2003002862
国際公開番号 WO2003076410
国際出願日 平成15年3月11日(2003.3.11)
国際公開日 平成15年9月18日(2003.9.18)
優先権データ
  • 2003JP002862 (2003.3.11) WO
  • 特願2002-066161 (2002.3.11) JP
発明の名称 (英語) Process for asymmetric intramolecular (3+2) cyclo-addition of hydrazones
発明の概要(英語) An intramolecular Ä3+2Ü cycloaddition reaction of a hydrazone is carried out under a mild condition with a high stereoselectivity and yield by reacting a hydrazone derivative in the presence of an asymmetric catalyst system obtained by mixing a zirconium alkoxide represented by the following formula (I): Zr(OR)4 (wherein R is a hydrocarbon group which may have a substituent) with a binaphthol derivative represented by the following formula (II): <CHEM> (wherein Y<1> and Y<2> are each identical or different and denote a hydrogen atom or a halogen atom, and at least one of Y<1> and Y<2> denotes a halogen atom).
特許請求の範囲(英語) [claim1]
1. A process for an asymmetric intramolecular [3+2] cycloaddition reaction of a hydrazone characterized by reacting a hydrazone derivative represented by the following formula (III): (see diagramm) wherein R **1, R **2, R **3 and R **4 are each methyl, R **5 is a benzoyl group which may have a substituent and X denotes CH 2, in the presence of an asymmetric catalyst system obtained by mixing a zirconium alkoxide represented by the following formula (I):

Zr(OR)4 (I)

wherein R is a hydrocarbon group which may have a substituent, with a binaphthol derivative represented by the following formula (II): (see diagramm) wherein Y **1 and Y **2 are each identical or different, Y **2 denotes a hydrogen atom or a halogen atom, and Y **1 denotes a halogen atom.
[claim2]
2. A process for an asymmetric intramolecular [3+2] cycloaddition reaction as claimed in claim 1, which is carried out in the presence of a primary alcohol.
[claim3]
3. A process for an asymmetric intramolecular [3+2] cycloaddition reaction as claimed in claim 2, wherein the primary alcohol is an n-propanol.
[claim4]
4. A process for an asymmetric intramolecular [3+2] cycloaddition reaction as claimed in any one of claims 1 to 3, by which an asymmetric cyclic compound represented by the following formula (IV): (see diagramm) is synthesized.
[claim5]
5. A process for an asymmetric intramolecular [3+2] cycloaddition reaction as claimed in any one of claims 1 to 4, wherein the zironium alkoxide used in the catalyst system is Zr(O **tBu) 4 or Zr(OPr) 4.
  • 出願人(英語)
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • 発明者(英語)
  • KOBAYASHI SHU
  • YAMASHITA YASUHIRO
  • ISHITANI HARURO
国際特許分類(IPC)
欧州特許分類/主・副
  • C07D231/56
指定国 Contracting States: DE FR GB
参考情報 (研究プロジェクト等) CREST Single Molecule and Atom Level Reactions AREA
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