Cobalt-Catalyzed Intramolecular Reactions between a Vinylcyclopropane and an Alkyne: Switchable [5+2] Cycloaddition and Homo-Ene Pathways

Chunlin Wu, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

Cobalt–diphosphine catalysts have been found to promote intramolecular reactions between a vinylcyclopropane and an alkyne to selectively afford either the [5+2] cycloaddition product or the homo-ene reaction product under solvent control. The former product is exclusively formed in noncoordinating 1,2-dichloroethane, whereas the latter is dominant in coordinating solvents, such as acetonitrile and dimethylacetamide. Furthermore, a highly enantioselective variant of the homo-ene reaction afforded chiral tetrahydrofuran, pyrrolidine, and cyclopentane derivatives bearing 1,3-diene and alkylidene substituents.

Original languageEnglish
Pages (from-to)6558-6562
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number22
DOIs
Publication statusPublished - 2018 May 28
Externally publishedYes

Keywords

  • asymmetric catalysis
  • cobalt
  • cycloaddition
  • cyclopropanes
  • C−C bond cleavage

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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