Chiral bisphosphazides as dual basic enantioselective catalysts

Hiroshi Naka, Nobuhiko Kanase, Masahiro Ueno, Yoshinori Kondo

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Chiral bisphosphazides complexed with lithium salts efficiently catalyze the direct enantioselective 1,4-addition of dialkyl malonates to acyclic enones. Spectroscopic studies on the stoichiometry of the bisphosphazide and lithium salt have indicated the formation of a 1:1 species as the active enantioselective catalyst. It is suggested that the catalyst generates a complex of the protonated phosphazide and the chiral nucleophile as the key intermediate. The phosphazide moiety appears to be a promising dual basic functionality for stereo- and chemoselective catalytic transformations.

Original languageEnglish
Pages (from-to)5267-5274
Number of pages8
JournalChemistry - A European Journal
Volume14
Issue number17
DOIs
Publication statusPublished - 2008 Jun 9

Keywords

  • Asymmetric catalysis
  • Basicity
  • Lithium
  • Michael addition
  • Phosphazene base

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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