Cobalt-Catalyzed Regio- and Diastereoselective Formal [3 + 2] Cycloaddition between Cyclopropanols and Allenes

Junfeng Yang, Qiao Sun, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

A cobalt-diphosphine catalyst has been found to promote a formal [3 + 2] cycloaddition reaction between a cyclopropanol and an allene via cyclopropanol ring opening, which affords a 3-alkylidenecyclopentanol derivative with high regio- and diastereoselectivities. The reaction tolerates monosubstituted, 1,1-disubstituted, and 1,3-disubstituted allenes and various functional groups. The reaction is proposed to proceed through carbometalation of the allene with a cobalt homoenolate followed by intramolecular carbonyl allylation of the resulting allylcobalt species.

Original languageEnglish
Pages (from-to)1973-1978
Number of pages6
JournalACS Catalysis
Volume9
Issue number3
DOIs
Publication statusPublished - 2019 Mar 1
Externally publishedYes

Keywords

  • allenes
  • cobalt catalysis
  • cycloaddition
  • cyclopropanes
  • homoenolate

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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