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Synthesis and structure of bridged thiazolium salts

✍ Scribed by Finian J. Leeper; David H.C. Smith

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
486 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

Bridged thiazolium salts (6a,b) have been synthesized using macrolactonisation techniques to make the corresponding thiazolinethiones (4a,b) followed by treatment with H202. For each compound the bridge exists predominantly in a single conformation which has been determined both by n.m.r. and X-ray crystallography.

Thiamin pyrophosphate is an important coenzyme involved in the decarboxylation of a-keto acids, in acyloin condensations, and in transketolization reactions. The same type of reactions are also catalysed non-enzymically by simple thiazolium salts or thiamin itself. In a few cases more complex catalysts have been employed in which

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Synthesis of and asymmetric induction by
Synthesis of and asymmetric induction by chiral polycyclic thiazolium salts
✍ A.Ulrich Gerhard; Finian J. Leeper πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 240 KB

Polycyclic thiazoles, 6a and b, have been synthesised and the enantiomers resolved. Alkylation gave chiral thiazolium salts which catalyse the dimerisation of benzaldehyde to give benzoin with enantiomefic excesses up to 26%. Reasons for these results are discussed.