Catalytic asymmetric Michael addition of nitroalkane to enone and enal

Masahiko Yamaguchi, Tai Shiraishi, Yoshihiro Igarashi, Masahiro Hirama

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123 Citations (Scopus)

Abstract

L-Proline rubidium salt catalyzes the asymmetric Michael addition of nitroalkanes to enones and an enal. (R)-Adducts were obtained from cyclic (Z)-enones and (S)-adducts from acyclic (E)-enones. Bu3SnH treatment of the products replaced the nitro group with hydrogen atom. The overall transformation allows the asymmetric alkylation of enones at the β-carbon atom.

Original languageEnglish
Pages (from-to)8233-8236
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number44
DOIs
Publication statusPublished - 1994 Oct 31

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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