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

被引：29

作者：

Andrés, C ^{[1
]}

Duque-Soladana, JP ^{[1
]}

Pedrosa, R ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 12期

关键词：

D O I：

10.1021/jo981693t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha,beta-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.

引用

页码：4282 / 4288

页数：7

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