Highly stereoselective Michael reduction/intramolecular Michael reaction cascade to synthesize trans-stereodiad comprising an all-carbon quaternary stereogenic center

Tomohiro Fujii, Kohei Orimoto, Masahisa Nakada

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A highly stereoselective Michael reduction/intramolecular Michael reaction cascade is described. The cascade is initiated by the regioselective Michael reduction of an α-methylidene ester with L-Selectride. This is followed by the highly stereoselective intramolecular Michael reaction which efficiently constructs a six-membered carbocyclic ring with formation of the trans-stereodiad, composed of an all-carbon quaternary center and a tertiary stereogenic center. The stereoselectivity is perfectly controlled by the choice of alkene geometry in the Michael acceptor.

Original languageEnglish
Pages (from-to)1100-1103
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number5
DOIs
Publication statusPublished - 2014 Jan 29

Keywords

  • Cascade
  • Intramolecular
  • Michael
  • Quaternary stereogenic center
  • Stereoselective

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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