B. Refouvelet, J. Robert, J. Couquelet
1994
Citations
0
Influential Citations
23
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
Thiazolidine-2,4-dicarboxylic acid 2 was obtained as a diastereoisomeric mixture from the condensation of glyoxylic acid with L(-)R-cysteine 1. In solution behaviour studies suggested that the reaction proceeded through an acid catalyzed epimerization mechanism. The methyl esterification of 2 was stereoselective, which can be explained by an interconversion of 2a via a ring seco intermediate. Condensation of the dimethyl ester 3 or the dissymmetric diester 4 with phenyl isocyanate gave rise to the same hydantoin 5. N-acylation of diesters 3 or 4 followed by the reaction with benzylamine was regioselective leading to bicyclic derivatives 8-10.