Asymmetric Michael Reaction of Aldehydes and α-Cyano α,β-Unsaturated Esters Catalyzed by Diphenylprolinol Silyl Ether; a Facile Asymmetric Route to 3,4,5-Trisubstituted Piperidines

Yujiro Hayashi, Amaechi Shedrack Odoh, Nektarios Kranidiotis-Hisatomi

Research output: Contribution to journalArticle

Abstract

A highly enantioselective diphenylprolinol silyl ether-mediated asymmetric Michael reaction of a variety of aldehydes and β-substituted α-cyano α,β-unsaturated esters was developed. The organocatalytic conjugate addition provided synthetically useful chiral adducts possessing three consecutive stereocenters and suitably oriented functional handles that were readily transformed via a sequence of reductive-cyclization and subsequent epimerization to furnish single isomers of 3,4,5-trisubstituted piperidines with high levels of yield and excellent enantiopurity.

Original languageEnglish
Pages (from-to)2412-2415
Number of pages4
JournalChemCatChem
Volume12
Issue number9
DOIs
Publication statusPublished - 2020 May 7

Keywords

  • Asymmetric synthesis
  • Michael reaction
  • Organocatalysis
  • Piperidine

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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