Aza-Henry reaction of ketimines catalyzed by guanidine and phosphazene bases

Nirmal K. Pahadi, Hitoshi Ube, Masahiro Terada

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

A general catalytic addition of nitromethane to simple N-diphenylphosphinoyl ketimines is achieved using either 10 mol % 1,1,3,3-tetramethylguanidine (TMG) or 10 mol % phosphazene (t-Bu-P1) as organic base catalysts in good to high yields. On the other hand, N-sulfinylketimines also furnished the aza-Henry product in good yield with moderate diastereoselectivity (3:1). Thus, the methodology developed here is a good template for developing the first organocatalytic approach towards the aza-Henry reaction of ketimines.

Original languageEnglish
Pages (from-to)8700-8703
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number49
DOIs
Publication statusPublished - 2007 Dec 3

Keywords

  • Aza-Henry reaction
  • Guanidine
  • Ketimine
  • Phosphazene

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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