The synthesis, N-alkylation and epimerisation study of a phthaloyl derived thiazolidine |
| |
Authors: | Emma B Veale |
| |
Institution: | School of Chemistry, Center for Synthesis and Chemical Biology, Trinity College Dublin, Dublin 2, Ireland |
| |
Abstract: | The synthesis of the phthaloyl protected thiazolidine, N-phthaloyl-methyl-2(R)-thiazolidine-4(R)-methyl ester, 2, and a study of its susceptibility to epimerise in a range of solvents, using 1H NMR spectroscopy, are described. Compound 2 was further reacted to yield the thiazole amino acid derivative, 3, and an N-alkylated thiazolidine derivative, 6, as a single diastereoisomer. The N-alkylation of 2, using mild bases, resulted in the formation of a mixture of diastereoisomers of 2 (2R,4R) and (2S,4R). Successful cleavage of the methyl ester and the phthaloyl protecting groups was achieved, giving rise to the formation of the two heterocyclic building blocks, 4 and 5. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|