Tetrahedron

The synthesis, N-alkylation and epimerisation study of a phthaloyl derived thiazolidine

EB Veale, JE O'Brien, T McCabe, T Gunnlaugsson

文献索引：Veale, Emma B.; O'Brien, John E.; McCabe, Thomas; Gunnlaugsson, Thorfinnur Tetrahedron, 2008 , vol. 64, # 28 p. 6794 - 6800

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被引用次数: 10

摘要

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 ...