Stereoselective synthesis of tetrasubstituted alkenes via torquoselectivity-controlled olefination of carbonyl compounds with ynolates

Mitsuru Shindo, Kenji Matsumoto

研究成果: 書籍/レポート タイプへの寄稿

32 被引用数 (Scopus)

抄録

The efficient synthesis of tetrasubstituted alkenes by the olefination of carbonyl compounds with ynolates is described. This reaction involves the cycloaddition of ynolates with carbonyl groups, followed by electrocyclic ring-opening of the resulting β-lactone enolates. Orbital symmetry during the electrocyclic ring opening requires conrotatory motion. The direction of this rotation (inward or outward) determines the E/Z geometry to the tetrasubstituted olefin product through torquoselectivity. Theoretical calculations revealed that several secondary orbital interactions are essential for the high torquoselectivity. This methodology is a novel olefination for constructing multisubstituted olefins.

本文言語英語
ホスト出版物のタイトルStereoselective Alkene Synthesis
編集者Jianbo Wang
ページ1-32
ページ数32
DOI
出版ステータス出版済み - 2012

出版物シリーズ

名前Topics in Current Chemistry
327
ISSN(印刷版)0340-1022

!!!All Science Journal Classification (ASJC) codes

  • 化学 (全般)

フィンガープリント

「Stereoselective synthesis of tetrasubstituted alkenes via torquoselectivity-controlled olefination of carbonyl compounds with ynolates」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル