Equatorial preference in the GaCl3-promoted ethenylation of cyclic ketones

M. Arisawa, C. Miyagawa, M. Yamaguchi

研究成果: Contribution to journalReview article査読

19 被引用数 (Scopus)

抄録

Silyl enol ethers derived from substituted cyclohexanones are ethenylated with trimethylsilylethyne in the presence of GaCl3. Carbon-carbon bond formation was completed in less than 5 min at room temperature and protodegallation of the organogallium intermediate formed with 6 M sulfuric acid gave β-enones. The reactions exhibit a bias for the equatorial C-C bond formation, which contrasts the axial stereochemistry of enolate alkylation. The origin of this stereoselectivity is discussed.

本文言語英語
ページ(範囲)138-145
ページ数8
ジャーナルSynthesis
1
DOI
出版ステータス出版済み - 2002
外部発表はい

All Science Journal Classification (ASJC) codes

  • 触媒
  • 有機化学

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