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

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journal contribution
posted on 22.05.1999, 00:00 by Celia Andrés, Juan P. Duque-Soladana, Rafael Pedrosa
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.