Direct asymmetric α-amination of cyclic ketones catalyzed by siloxyproline

Yujiro Hayashi, Seiji Aratake, Yoshinaga Imai, Kazuhiro Hibino, Qi Yin Chen, Junichiro Yamaguchi, Tadafumi Uchimaru

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

trans-tert-Butyldimethylsiloxy-l-proline displays greater catalytic activity and affords higher enantioselectivity than the parent proline in the a-amination reaction of carbonyl compounds with azodicarboxylate. A quantum mechanical calculation reveals the structure of the transition state. In the presence of a catalytic amount of siloxyproline and water (3-9 equiv), α-amino carbonyl derivatives, which are important synthetic intermediates, are obtained in good yield and with excellent enantioselectivity.

Original languageEnglish
Pages (from-to)225-232
Number of pages8
JournalChemistry - An Asian Journal
Volume3
Issue number2
DOIs
Publication statusPublished - 2008 Feb 1

Keywords

  • Amination
  • Asymmetric synthesis
  • Organocatalysis
  • Proline
  • Siloxyproline

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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