Tetrahedron

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

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

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

Full Text: HTML

Citation Number: 10

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 ...

Related Articles:

Synthesis of some analogues of (±) gelliusine F,(±) gelliusine E, and total synthesis of 2, 2-di (6′-bromo-3′-indolyl) ethylamine

[Seetham Naidu; Bhuyan, Pulak J. Tetrahedron Letters, 2012 , vol. 53, # 4 p. 426 - 428]

Total synthesis and absolute configuration of malyngamide W

[Qi, Xian-Liang; Zhang, Jun-Tao; Feng, Jian-Peng; Cao, Xiao-Ping Organic and Biomolecular Chemistry, 2011 , vol. 9, # 10 p. 3817 - 3824]

Novel Approach to the Synthesis of (R, S)??Baclofen via PD (II)??Bipyridine–Catalyzed Conjugative Addition

[Varala, Ravi; Adapa, Srinivas R. Synthetic Communications, 2006 , vol. 36, # 24 p. 3743 - 3747]

Biosynthese von Naturstoffen mit einer P C??Bindung, II. Hydroxylierung von deuterierten (2??Aminoethyl) phosphonsäuren zu (2??Amino??1??hydroxyethyl) …

[Hammerschmidt, Friedrich Liebigs Annalen der Chemie, 1988 , p. 537 - 542]

More Articles...