Asymmetric Diels–Alder Reaction of Acrylamides Having <i>trans</i>-2,5-Disubstituted Pyrrolidines as Chiral Auxiliaries

Abstract

Abstract The asymmetric Diels–Alder reaction between chiral acrylamides derived from (2R,5R)-2,5-disubstituted pyrrolidines and cyclopentadiene gave (1R,2R,4R)-5-norbornene-2-carboxylic acid amides 3a–c with excellent diastereoface selectivity. The amides 3a–c were converted into the corresponding carboxylic acid by an iodolactonization-reduction sequence and 2,5-disubstituted pyrrolidines were recovered intact.