Cobalt-Catalyzed Enantioselective and Chemodivergent Addition of Cyclopropanols to Oxabicyclic Alkenes

Junfeng Yang, Yoshiya Sekiguchi, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

We report herein cobalt-catalyzed enantioselective and chemodivergent reactions between a cyclopropanol and an oxabicyclic alkene via a cobalt homoenolate, which afford either an alkylative ring-opening product or a hydroalkylation product, with the counterion of the cobalt catalyst being a major chemoselectivity-controlling factor. A catalyst generated from cobalt(II) chloride and a chiral diphosphine promotes alkylative ring opening to afford 1,2-dihydronaphthalen-1-ol derivatives in good yields with high enantioselectivity. By contrast, a catalyst generated from cobalt(II) acetate and the same diphosphine ligand, with the assistance of methanol, selectively affords hydroalkylation products with retention of the bicyclic structure at a comparable level of enantioselectivity.

Original languageEnglish
Pages (from-to)5638-5644
Number of pages7
JournalACS Catalysis
Volume9
Issue number6
DOIs
Publication statusPublished - 2019 Jun 7
Externally publishedYes

Keywords

  • asymmetric catalysis
  • cobalt catalysis
  • cyclopropanes
  • desymmetrization
  • homoenolate

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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