A Novel Approach to Chiral, Nonracemic Pyrrolidines by 5-exo-trig Diastereoselective Radical Cyclization on Acrylamides Derived from (-)-8-Aminomenthol

…, JP Duque-Soladana, R Pedrosa

文献索引：Andres, Celia; Duque-Soladana, Juan P.; Pedrosa, Rafael Journal of Organic Chemistry, 1999 , vol. 64, # 12 p. 4282 - 4288

全文：HTML全文

被引用次数: 29

摘要

α, β-Unsaturated amides supported on perhydro-1, 3-benzoxazines derived from (-)-8- aminomenthol as chiral auxiliaries undergo regio-and stereoselective 5-exo-trig radical cyclization leading to diastereomeric five-membered lactams. These cyclization products are transformed into enantiopure 3, 4-disubstituted pyrrolidines by reduction with aluminum hydride followed by removal of the menthol appendage.