A Catalytic Enantioselective Michael Addition of a Simple Malonate to Prochiral α,β‐Unsaturated Ketoses and Aldehydes

Masahiko Yamaguchi, Tai Shiraishi, Masahiro Hirama

Research output: Contribution to journalArticle

167 Citations (Scopus)

Abstract

Enantiomeric excesses of up to 77% ee can be achieved in the Michael addition of diisopropyl malonate to enones and enals in the presence of 5 mol % of the rubidium salt of L‐proline (which contains a small amount of water) as catalyst. The absolute configurations of the products show that the nucleophile always attacks from the same side of the CO plane irrespective of the configuration of the CC bond. (Figure Presented.)

Original languageEnglish
Pages (from-to)1176-1178
Number of pages3
JournalAngewandte Chemie International Edition in English
Volume32
Issue number8
DOIs
Publication statusPublished - 1993 Jan 1

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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