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

Org Lett

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

Published: December 2005

[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.

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http://dx.doi.org/10.1021/ol0513692DOI Listing

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