Torquoselective olefination of carbonyl compounds with ynolates: Highly efficient stereoselective synthesis of tetrasubstituted alkenes

Mitsuru Shindo, Seiji Mori

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

The torquoselectivity-controlled olefination of carbonyl compounds with ynolates affording tetrasubstituted alkenes is described. The E/Z selectivity is determined in the step consisting of electrocyclic ring opening of the β-lactone enolates (oxetenes) derived from cycloaddition of ynolates with carbonyl compounds. Theoretical calculations revealed that several secondary orbital interactions are critical for the high torquoselectivity. This methodology is a novel olefination for constructing multisubstituted olefins.

Original languageEnglish
Pages (from-to)2231-2243
Number of pages13
JournalSynlett
Issue number15
DOIs
Publication statusPublished - Sep 15 2008

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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