The synthesis, N-alkylation and epimerisation study of a phthaloyl derived thiazolidine
作者： Emma B. Veale , John E. O'Brien , Thomas McCabe , Thorfinnur Gunnlaugsson
DOI: 10.1016/J.TET.2008.04.097
关键词: Amino acid derivative 、 Chemistry 、 Thiazole 、 Thiazolidine 、 Alkylation 、 Stereochemistry 、 Cleavage (embryo) 、 Derivative (chemistry) 、 Yield (chemistry) 、 Diastereomer
摘要: Abstract The synthesis of the phthaloyl protected thiazolidine, N-phthaloyl-methyl-2(R)-thiazolidine-4(R)-methyl ester, 2, and a study its susceptibility to epimerise in range solvents, using 1H NMR spectroscopy, are described. Compound 2 was further reacted yield thiazole amino acid derivative, 3, an N-alkylated thiazolidine 6, as single diastereoisomer. N-alkylation mild bases, resulted formation mixture diastereoisomers (2R,4R) (2S,4R). Successful cleavage methyl ester protecting groups achieved, giving rise two heterocyclic building blocks, 4 5.
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