Copper-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Imino Esters to Unsaturated Sultones

Shohei Furuya; Kazuya Kanemoto; Shin-Ichi Fukuzawa

doi:10.1021/acs.joc.0c01023

Copper-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Imino Esters to Unsaturated Sultones

J Org Chem. 2020 Jun 19;85(12):8142-8148. doi: 10.1021/acs.joc.0c01023. Epub 2020 Jun 8.

Authors

Shohei Furuya¹, Kazuya Kanemoto¹, Shin-Ichi Fukuzawa¹

Affiliation

¹ Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.

PMID: 32468817
DOI: 10.1021/acs.joc.0c01023

Abstract

The asymmetric 1,3-dipolar cycloaddition of glycine imino esters to 1-propene-1,3-sultone or sulfocoumarins is described. The reaction was efficiently catalyzed by Cu(MeCN)₄BF₄/DTBM-Segphos or Cu(MeCN)₄BF₄/tBu-FcPhox at room temperature to afford fused pyrrolidines as single regioisomers with excellent diastereoselectivity and enantioselectivity. The broad substrate scope of this reaction provides convenient access to structurally diverse multisubstituted pyrrolidines in an optically pure fashion.

Publication types

Research Support, Non-U.S. Gov't