Phosphine-Catalyzed Enantioselective (3+2) Annulation of Vinylcyclopropanes with Imines for the Synthesis of Chiral Pyrrolidines

Fuhao Zhang, Xuan Dai, Lei Dai, Wenrui Zheng, Wai Lun Chan, Xiaodong Tang, Xumu Zhang, Yixin Lu

Research output: Journal article publicationJournal articleAcademic researchpeer-review

3 Citations (Scopus)

Abstract

A phosphine-catalyzed highly enantioselective and diastereoselective (up to 98 % ee and >20 : 1 dr) (3+2) annulation between vinylcyclopropanes and N-tosylaldimines has been developed, which allows facile access to a range of highly functionalized chiral pyrrolidines. Notably, this method makes use of vinylcyclopropanes as a synthon for phosphine-mediated asymmetric annulation reaction, which will offer new opportunities for potential applications of cyclopropanes substrates in phosphine-catalyzed organic transformations.

Original languageEnglish
Article numbere202203212
JournalAngewandte Chemie - International Edition
Volume61
Issue number24
DOIs
Publication statusPublished - 13 Jun 2022
Externally publishedYes

Keywords

  • Annulation
  • Enantioselective
  • Phosphine Catalysis
  • Pyrrolidines
  • Vinylcyclopropanes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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