The synthesis and stereochemistry of new 2-substituted 4-thiazolidine acetic acids

Article abstract of DOI:10.1016/S0040-4020(01)96157-5

Reaction of isopropylidene-protected β-homopenicillamine 2 with various aldehydes leads to a number of new 2-monosubstituted 4-thiazolidine acetic acids 4. Thiazolidines 4 are formed with high diastereoselectivity. Assignment of configuration is made by NMR-analysis. The diastereomeric pure compound 4 possess unstable chiral centers in position 2 and undergo rapid epimerisation in solution at higher temperatures.