Direct Asymmetric Michael Reaction of α,β-Unsaturated Aldehydes and Ketones Catalyzed by Two Secondary Amine Catalysts

Yujiro Hayashi, Nariyoshi Umekubo

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

A direct asymmetric Michael reaction of α,β-unsaturated aldehydes and ketones proceeded in the presence of two pyrrolidine-type catalysts, a diphenylprolinol silyl ether and hydroxyproline, to afford synthetically useful δ-keto aldehydes with excellent diastereo- and enantioselectivity. Although there are several iminium ions and enamines in the reaction mixture, the iminium ion generated by the former catalyst reacts preferentially with the enamine generated by the latter catalyst.

Original languageEnglish
Pages (from-to)1958-1962
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number7
DOIs
Publication statusPublished - 2018 Feb 12

Keywords

  • Michael reaction
  • asymmetric synthesis
  • enamines
  • organocatalysis
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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