Asymmetric Michael addition of nitroalkanes to prochiral acceptors catalyzed by proline rubidium salts

Masahiko Yamaguchi, Yoshihiro Igarashi, Ravinder S. Reddy, Tai Shiraishi, Masahiro Hirama

Research output: Contribution to journalArticlepeer-review

129 Citations (Scopus)

Abstract

Proline rubidium salts catalyze the asymmetric Michael addition of nitroalkanes to prochiral accepters. When(2S)-L-prolines were used, acyclic (E)-enones gave (S)-adducts and cyclic (Z)-enones gave (R)-adducts predominantly. Enantiomeric excesses exceeding 80% were attained in some reactions of secondary nitroalkanes. Primary nitroalkanes gave mixtures of diastereomers which possess the same configuration at the β-carbon atom. The nitro group of the adducts can be replaced with hydrogen by Bu3SnH reduction. The overall transformation is equivalent to an asymmetric β-alkylation of the enone. Functionalized nitroalkanes such as nitro alcohol, nitro ester, and nitroalkene may also be utilized in the reaction.

Original languageEnglish
Pages (from-to)11223-11236
Number of pages14
JournalTetrahedron
Volume53
Issue number32
DOIs
Publication statusPublished - 1997 Aug 11

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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