Copper(I)-catalyzed enantioselective synthesis of α-chiral linear or carbocyclic (e)-(γ-alkoxyallyl)boronates

Eiji Yamamoto, Yuta Takenouchi, Taichi Ozaki, Takanori Miya, Hajime Ito

研究成果: ジャーナルへの寄稿学術誌査読

67 被引用数 (Scopus)

抄録

A new method has been developed for the catalytic asymmetric synthesis of α-chiral linear or carbocyclic (γ-alkoxyallyl)boronates via the copper(I)-catalyzed γ-boryl substitution of allyl acetals. This reaction afforded the products in high yields with excellent E:Z selectivities and enantioselectivities [only (E)-product, 91-98% ee] and also exhibited high functional group compatibility. Subsequent allylation of aldehydes with the α-chiral (γ-alkoxyallyl)boronates provided the anti-1,2-diol derivatives in a highly stereospecific manner, and the utility of the α-chiral (γ-alkoxyallyl)boronates was further demonstrated by a convergent coupling of a complex polyol derivative using a (γ-alkoxyallyl)boronate and a chiral α-oxyaldehyde. The stereoselective modular construction of a complex 3,3-disubstituted cyclopentene containing three consecutive stereocenters including a quaternary chiral carbon was also reported. Useful transformations of the α-chiral linear (γ-alkoxyallyl)boronates were also demonstrated.

本文言語英語
ページ(範囲)16515-16521
ページ数7
ジャーナルJournal of the American Chemical Society
136
47
DOI
出版ステータス出版済み - 11月 26 2014
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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