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Process for asymmetric intramolecular [3+2] cyclo-addition of hydrazones

外国特許コード F110005101
整理番号 A051-88US
掲載日 2011年8月23日
出願国 アメリカ合衆国
出願番号 50730903
公報番号 20050165237
公報番号 7351831
出願日 平成15年3月11日(2003.3.11)
公報発行日 平成17年7月28日(2005.7.28)
公報発行日 平成20年4月1日(2008.4.1)
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
  • 特願2002-066161 (2002.3.11) JP
  • 2003WO-JP02862 (2003.3.11) WO
発明の名称 (英語) Process for asymmetric intramolecular [3+2] cyclo-addition of hydrazones
発明の概要(英語) (US7351831)
An intramolecular [3+2] 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): <?in-line-formulae description="In-line Formulae" end="lead"?>Zr(OR)<sub>4</sub> (I)<?in-line-formulae description="In-line Formulae" end="tail"?> (wherein R is a hydrocarbon group which may have a substituent) with a binaphthol derivative represented by the following formula (II): (wherein Y<sup>1 </sup>and Y<sup>2 </sup>are each identical or different and denote a hydrogen atom or a halogen atom, and at least one of Y<sup>1 </sup>and Y<sup>2 </sup>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 which comprises reacting a hydrazone derivative represented by the following formula (III):
wherein R1, R2, R3, R4 and R5 are each identical or different and denote a hydrogen atom or a hydrocarbon group which may have a substituent or a hetero atom, R1 and R2, R3 and R4 may be linked to form a ring by a hydrocarbon chain which may have a substituent or a hydrocarbon chain which has a hetero atom, and X denotes a hetero atom or a hydrocarbon chain which may have a substituent or a hetero atom, 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):
andwherein Y1 and Y2 are each identical or different and denote a hydrogen atom or a halogen atom, and at least one of Y1 and Y2 denotes a halogen atom, to produce a cycloaddition reaction product.
[claim2]
2. The process for an asymmetric intramolecular [3+2] cycloaddition reaction according to claim 1, which is carried out in the coexistence of a primary alcohol.
[claim3]
3. The process for an asymmetric intramolecular [3+2] cycloaddition reaction according to claim 2, wherein the primary alcohol is an n-propanol.
[claim4]
4. The process for an asymmetric intramolecular [3+2] cycloaddition reaction according to claim 1, by which an asymmetric cyclic compound represented by the following formula (IV):
is synthesized.
[claim5]
5. The process for an asymmetric intramolecular [3+2] cycloaddition reaction according to claim 1, wherein the zirconium alkoxide used in the catalyst system is Zr(OtBu)4 or Zr(OPr)4.
  • 発明者/出願人(英語)
  • KOBAYASHI SHU
  • YAMASHITA YASUHIRO
  • ISHITANI HARURO
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
米国特許分類/主・副
  • 546/119
  • 546/17
  • 548/357.5
  • 548/360.1
  • 548/360.5
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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