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

研究成果: ジャーナルへの寄稿学術誌査読

7 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ(範囲)8832-8838
ページ数7
ジャーナルTetrahedron
65
43
DOI
出版ステータス出版済み - 10月 24 2009

!!!All Science Journal Classification (ASJC) codes

  • 生化学
  • 創薬
  • 有機化学

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