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

Nariyoshi Umekubo, Yujiro Hayashi

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6 Citations (Scopus)


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
Issue number34
Publication statusPublished - 2020 Sept 14


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


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