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

Mitsuru Shindo, Seiji Mori

研究成果: Contribution to journalArticle査読

38 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ(範囲)2231-2243
ページ数13
ジャーナルSynlett
15
DOI
出版ステータス出版済み - 9 15 2008

All Science Journal Classification (ASJC) codes

  • 有機化学

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