A novel approach to chiral, nonracemic pyrrolidines by 5-exo-trig diastereoselective radical cyclization on acrylamides derived from(-)-8-aminomenthol

Authors
Andres, C Duque-Soladana, JP Pedrosa, R
Citation
C. Andres et al., A novel approach to chiral, nonracemic pyrrolidines by 5-exo-trig diastereoselective radical cyclization on acrylamides derived from(-)-8-aminomenthol, J ORG CHEM, 64(12), 1999, pp. 4282-4288
Citations number
41
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
12
Year of publication
1999
Pages
4282 - 4288
Database
ISI
SICI code
0022-3263(19990611)64:12<4282:ANATCN>2.0.ZU;2-I
Abstract
alpha,beta-Unsaturated amides supported on perhydro-1,3-benzoxazines derive d from (-)-8-aminomenthol as chiral auxiliaries undergo regio- and stereose lective 5-exo-trig radical cyclization leading to diastereomeric five-membe red lactams. These cyclization products are transformed into enantiopure 3, 4-disubstituted pyrrolidines by reduction with aluminum hydride followed by removal of the menthol appendage.