Nickel-Catalyzed Ring-Opening Allylation of Cyclopropanols via Homoenolate

Yoshiya Sekiguchi, Yan Ying Lee, Naohiko Yoshikai

研究成果: Article査読

3 被引用数 (Scopus)

抄録

We report herein a nickel-catalyzed ring-opening allylation of cyclopropanols with allylic carbonates that occurs under mild and neutral conditions. The reaction displays linear selectivity for both linear and branched acyclic allylic carbonates and is also applicable to cyclic allylic carbonates, affording a variety of δ,ϵ-unsaturated ketones in moderate to good yields. Mechanistic experiments are in accord with a catalytic cycle involving decarboxylative oxidative addition of allylic carbonate to Ni(0), alkoxide exchange with cyclopropanol, cyclopropoxide-to-homoenolate conversion on Ni(II), and C-C reductive elimination.

本文言語English
ページ(範囲)5993-5997
ページ数5
ジャーナルOrganic letters
23
15
DOI
出版ステータスPublished - 2021 8 6

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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