Synthesis 2005(6): 945-956  
DOI: 10.1055/s-2005-861838
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Polysubstituted Pyrrolidines from Aminonitriles

Nino Meyer, Frank Werner, Till Opatz*
Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
Fax: +49(6131)3924786; e-Mail: opatz@uni-mainz.de;
Further Information

Publication History

Received 15 October 2004
Publication Date:
21 February 2005 (eFirst)

Abstract

α-Aminonitriles with a mono- or unsubstituted amino group as well as α-(alkylideneamino)nitriles can be employed as easily accessible α-aminocarbanion equivalents. Their α-deprotonation yields stabilized carbanions, which undergo smooth 1,4-addition to α,β-unsaturated carbonyl compounds. The resulting δ-keto-α-aminonitriles can be reductively cyclized to form polysubstituted pyrrolidines.