155266-94-7Relevant academic research and scientific papers
3-Aminoacetylthiazolidine-4-carboxylate Esters and their 1-Thia-4-azaspiro[4.5]decane-3-carboxylate Derivatives. Synthesis and Stereochemical Properties
Pellegrini,Refouvelet,Dachet,Rouland,Robert
, p. 1685 - 1691 (2007/10/03)
Dimethyl thiazolidine-2,4-dicarboxylate 2 and ethyl 1-thia-4-azaspiro[4.5]decane-3-carboxylates 3-5 were obtained as a diastereoisomeric mixture while their 3-aminoacetyl derivatives were isolated in only one isomeric form. These reactions of N-acylation were stereoselective, which can be explained by an interconversion of the diastereoisomers via a seco intermediate. The 1H nmr analysis of amides 6 and 11 exhibited the presence of both cis and irons amide bond conformations, whereas only one cis conformation was observed for spiro amides 8-10 and 13-15.
Thiazolidine-2,4-dicarboxylic acid and its esters: Synthesis, in solution behaviour and regioselective cyclocondesation
Refouvelet,Robert,Couquelet,Tronche
, p. 77 - 80 (2007/10/02)
Thiazolidine-2,4-dicarboxylic acid 2 was obtained as a diastereoisomeric mixture from the condensation of glyoxylic acid with L(-)R-cysteine Σ. 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 3-10.
