New stereoselective synthesis of trans-2,5-disubstituted pyrrolidines by cyclization of aminyl radicals generated from 2- and/or 5-substituted N-chloro-N-alkylalk-4-enylamines with Bu3SnH-azoisobutyronitrile
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 777-778
- https://doi.org/10.1039/p19940000777
Abstract
trans-N-Alkyl-2- and/or 5-substituted pyrrolidines are stereoselectively formed in up to 63% yields by N-chlorination of 2- and/or 5-substituted N-methylpent-4-enylamine with N-chlorosuccinimide, followed by heating a solution of the resulting N-chloro-unsaturated amines in benzene with Bu3SnH–azoisobutyronitrile under reflux; a pathway involving stereoselective cyclization of neutral aminyl radicals is proposed.Keywords
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