title: Enantioselective Michael reactions of chiral secondary enaminoesters with 2-substituted nitroethylenes. Syntheses of trans, trans-2,4-disubstituted pyrrolidine-3-carboxylates
abstract: The Michael reaction of chiral 3-substituted secondary enaminoesters with 2-substituted nitroethylenes leads to (Z)-adducts, with good to excellent diastereoselectivity. The nitro group of these adducts was catalytically reduced to give, after cyclization and chiral amine elimination, pyrrolines or pyrrolidines after further reduction. In particular, the syntheses of ethyl (2R,3S,4S)-2,4-dimethylpyrrolidine-3-carboxylate and ethyl (2R,3R,4S)-2-(4-methoxyphenyl)-4-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate are described.
authors.affiliation: Laboratoire de Chimie Organique, CNRS (ESA 7084), ESPCI, Paris, France.
authors.initials: G
authors.lastname: Revial
authors.initials: S
authors.lastname: Lim
authors.initials: B
authors.lastname: Viossat
authors.initials: P
authors.lastname: Lemoine
authors.initials: A
authors.lastname: Tomas
authors.initials: AF
authors.lastname: Duprat
authors.initials: M
authors.lastname: Pfau