Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines

Hitoshi Ube, Masahiro Terada

Research output: Contribution to journalArticle

59 Citations (Scopus)

Abstract

The enantioselective activation of nitroalkanes was attempted on the basis of the complexation between chiral guanidinium and nitronate through two hydrogen bonds. The proposed enantioselective activation was applied to the diastereo- and enantioselective Henry (nitroaldol) reaction of nitroalkanes with aldehydes using axially chiral guanidine bases as the catalyst. Optically active nitroaldol products were obtained in acceptable yields with fairly good enantio- and diastereoselectivities at low temperature.

Original languageEnglish
Pages (from-to)3895-3898
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number14
DOIs
Publication statusPublished - 2009 Jul 15

Keywords

  • Asymmetric catalysis
  • Guanidine
  • Henry reaction
  • Nitroaldol reaction
  • Organocatalysis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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