A formal [3+2] cycloaddition process with nonactivated aziridines to polysubstituted indolizidines

Wei Zhu; Guorong Cai; Dawei Ma

doi:10.1021/ol0513692

A formal [3+2] cycloaddition process with nonactivated aziridines to polysubstituted indolizidines

Org Lett. 2005 Dec 8;7(25):5545-8. doi: 10.1021/ol0513692.

Authors

Wei Zhu¹, Guorong Cai, Dawei Ma

Affiliation

¹ State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.

PMID: 16320987
DOI: 10.1021/ol0513692

Abstract

[chemical reaction: see text]. Heating a mixture of ethyl 7-iodo-2-heptynoate (or its analogues), 2-aryl aziridines, and K2CO3 in dry CH(3)CN delivers polysubstituted indolizidines. This reaction goes through an S(N)2/formal [3+2] cycloaddition process and represents the first synthetically useful example of the formal [3+2] cycloaddition process through a C-N bond cleavage of nonactivated aziridines.