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. 2022 Jun 13;61(24):e202203212.
doi: 10.1002/anie.202203212. Epub 2022 Apr 19.

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

Fuhao Zhang  1   2 , Xuan Dai  1 , Lei Dai  1 , Wenrui Zheng  1 , Wai-Lun Chan  1 , Xiaodong Tang  1 , Xumu Zhang  2 , Yixin Lu  1
Affiliations

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

Fuhao Zhang et al. Angew Chem Int Ed Engl. .

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.

Keywords: Annulation; Enantioselective; Phosphine Catalysis; Pyrrolidines; Vinylcyclopropanes.

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