The effects of C-S and C-Se bonds on torquoselectivity: stereoselective olefination of α-thio and α-selenoketones with ynolates

Takashi Yoshikawa, Seiji Mori, Mitsuru Shindo

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Highly Z-selective olefination of acyclic α-thio and α-selenoketones with ynolates has been achieved, and the theoretical calculations of the transition states in the ring-opening of the intermediates, the β-lactone enolates, revealed that the torquoselectivity was controlled by the secondary orbital interactions between the σ orbital of the C-S bond or a lone pair orbital on the S and σ* orbitals of the breaking C-O bond, and the σ orbital of the breaking C-O bond or a lone pair orbital on the O on the ring and the σ* orbitals of the C-S bond. The synthetic applications of the resulting olefins are also shown.

Original languageEnglish
Pages (from-to)8832-8838
Number of pages7
JournalTetrahedron
Volume65
Issue number43
DOIs
Publication statusPublished - Oct 24 2009

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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