Asymmetric One-Pot Mukaiyama Michael/Michael Reaction Catalyzed by Diphenylprolinol Silyl Ether

Nariyoshi Umekubo, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The asymmetric catalytic Mukaiyama Michael reaction between α,β-unsaturated aldehydes and silyl enol ether derived from a cyclic ketone was catalyzed by diphenylprolinol silyl ether to afford Michael products with excellent diastereo- and enantioselectivities. Bicyclo[2.2.2]octanone derivatives can be synthesized as a single isomer in a nearly optically pure form via a two-step, one-pot reaction, comprising the sequential Mukaiyama Michael reaction and intramolecular Michael reaction starting from dienol silyl ether and α,β-unsaturated aldehydes, catalyzed by diphenylprolinol silyl ether. In the second Michael reaction, positive kinetic resolution occurred to increase the enantioselectivity.

Original languageEnglish
Pages (from-to)5596-5600
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number34
DOIs
Publication statusPublished - 2020 Sep 14

Keywords

  • Asymmetric reactions
  • Kinetic resolution
  • Mukaiyama Michael reaction
  • One-pot reactions
  • Organocatalysis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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