Synthesis of Bicyclo[2.2.2]octanes with a Quaternary Bridgehead Carbon by Diphenylprolinol Silyl Ether-mediated Domino Reaction

Nariyoshi Umekubo, Tohru Taniguchi, Kenji Monde, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

Abstract

Bicyclo[2.2.2]octane derivatives possessing a quaternary bridgehead carbon were synthesized with excellent diastereoselectivity in nearly optically pure form by diphenylprolinol silyl ether mediated domino Michael/Michael reaction of α,β-unsaturated aldehyde and cyclohex-2-en-1-one bearing an electron-withdrawing group at the 3-position. Carbonitrile, alkoxycarbonyl, and sulfonyl substituents were successfully employed as a suitable electron-withdrawing group at the 3-position of cyclohex-2-en-1-one.

Original languageEnglish
JournalAsian Journal of Organic Chemistry
DOIs
Publication statusAccepted/In press - 2021

Keywords

  • asymmetric synthesis
  • domino reaction
  • Michael reaction
  • organocatalyst
  • quaternary carbon

ASJC Scopus subject areas

  • Organic Chemistry

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