J. Zhuo, D. Burns, Colin Zhang
Feb 1, 2007
Citations
0
Influential Citations
11
Citations
Journal
Synlett
Abstract
An efficient asymmetric synthesis of conformationally constrained (2S,3S)-piperidinedicarboxylic acid derivatives starting from L-aspartic acid β-tert-butyl ester and 3-chloro-2-(chloromethyl)-1-propene is described. The key steps involve N-alkylation of the aspartic acid ester followed by a stereoselective enolate intramolecular cyclization (>95:5 dr). Various synthetic strategies were explored to achieve the cyclopropanation of the resulting olefin, including the Simmons-Smith reaction and palladium-catalyzed cyclopropanation.