Nickel-Catalyzed Ring-Opening Allylation of Cyclopropanols via Homoenolate

Yoshiya Sekiguchi, Yan Ying Lee, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)5993-5997
Number of pages5
JournalOrganic letters
Volume23
Issue number15
DOIs
Publication statusPublished - 2021 Aug 6

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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