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.
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Andrés et al. (1999) studied this question.
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