HIGHLY DIASTEREOSELECTIVE FORMATION OF SUBSTITUTED INDOLIZIDINES AND QUINOLIZIDINES BY RADICAL CYCLIZATION

Authors
BECKWITH ALJ JOSEPH SP MAYADUNNE RTA
Citation
Alj. Beckwith et al., HIGHLY DIASTEREOSELECTIVE FORMATION OF SUBSTITUTED INDOLIZIDINES AND QUINOLIZIDINES BY RADICAL CYCLIZATION, Journal of organic chemistry, 58(16), 1993, pp. 4198-4199
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
58
Issue
16
Year of publication
1993
Pages
4198 - 4199
Database
ISI
SICI code
0022-3263(1993)58:16<4198:HDFOSI>2.0.ZU;2-W
Abstract
2-Substituted 2,3-dihydro-4-pyridinones (eg., 1a) bearing an (omega-br omoacyl)-, (o-bromoaroyl)-, or (o-bromophenyl)aeetyl group on nitrogen , when treated with tributylstannane, undergo highly diastereoselectiv e cyclization by intramolecular homolytic addition anti to the substit uent at C-2; molecular mechanics calculation support the view that the diastereoselectivity arises from the nonbonded interaction between th e substituent and the amide carbonyl group.