Reversible 1,3-anti/syn-stereochemical courses in copper-catalyzed γ-selective allyl-alkyl coupling between chiral allylic phosphates and alkylboranes

Kazunori Nagao, Umi Yokobori, Yusuke Makida, Hirohisa Ohmiya, Masaya Sawamura

研究成果: Contribution to journalArticle査読

48 被引用数 (Scopus)

抄録

The stereochemical courses of the copper-catalyzed allyl-alkyl coupling between enantioenriched chiral allylic phosphates and alkylboranes were switchable between 1,3-anti and 1,3-syn selectivities by the choice of solvents and achiral alkoxide bases with different steric demands. The reactions with γ-silylated allylic phosphates allow efficient synthesis of enantioenriched chiral allylsilanes with tertiary or quaternary carbon stereogenic centers. Cyclic and acyclic bimodal participation of alkoxyborane species in an organocopper addition-elimination sequence is proposed to account for the phenomenon of the anti/syn-stereochemical reversal.

本文言語英語
ページ(範囲)8982-8987
ページ数6
ジャーナルJournal of the American Chemical Society
134
21
DOI
出版ステータス出版済み - 5 30 2012
外部発表はい

All Science Journal Classification (ASJC) codes

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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