Enantioselective Michael reactions of chiral secondary enaminoesters with 2-substituted nitroethylenes. Syntheses of trans, trans-2,4-disubstituted pyrrolidine-3-carboxylates

G Revial; S Lim; B Viossat; P Lemoine; A Tomas; AF Duprat; M Pfau

doi:10.1021/jo000206i

Enantioselective Michael reactions of chiral secondary enaminoesters with 2-substituted nitroethylenes. Syntheses of trans, trans-2,4-disubstituted pyrrolidine-3-carboxylates

J Org Chem. 2000 Jul 28;65(15):4593-600. doi: 10.1021/jo000206i.

Authors

G Revial¹, S Lim, B Viossat, P Lemoine, A Tomas, AF Duprat, M Pfau

Affiliation

¹ Laboratoire de Chimie Organique, CNRS (ESA 7084), ESPCI, Paris, France.

PMID: 10959864
DOI: 10.1021/jo000206i

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.