NEW STEREOSELECTIVE SYNTHESIS OF TRANS-2,5-DISUBSTITUTED PYRROLIDINESBY CYCLIZATION OF AMINYL RADICALS GENERATED FROM 2-SUBSTITUTED AND OR5-SUBSTITUTED N-CHLORO-N-ALKYLALK-4-ENYLAMINES WITH BU(3)SNH-AZOISOBUTYRONITRILE/

Authors
TOKUDA M FUJITA H SUGINOME H
Citation
M. Tokuda et al., NEW STEREOSELECTIVE SYNTHESIS OF TRANS-2,5-DISUBSTITUTED PYRROLIDINESBY CYCLIZATION OF AMINYL RADICALS GENERATED FROM 2-SUBSTITUTED AND OR5-SUBSTITUTED N-CHLORO-N-ALKYLALK-4-ENYLAMINES WITH BU(3)SNH-AZOISOBUTYRONITRILE/, Journal of the Chemical Society. Perkin transactions. I, (7), 1994, pp. 777-778
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
7
Year of publication
1994
Pages
777 - 778
Database
ISI
SICI code
0300-922X(1994):7<777:NSSOTP>2.0.ZU;2-U
Abstract
trans-N-Alkyl-2- and/or 5-substituted pyrrolidines are stereoselective ly formed in up to 63% yields by N-chlorination of 2- and/or 5-substit uted N-methylpent-4-enylamine with N-chloro-succinimide, followed by h eating a solution of the resulting N-chloro-unsaturated amines in benz ene with Bu(3)SnH-azoisobutyronitrile under reflux; a pathway involvin g stereoselective cyclization of neutral aminyl radicals is proposed.