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Synthesis 1999; 1999(5): 839-843
DOI: 10.1055/s-1999-3474
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Synthesis of Diastereomerically Pure [1,3]Thiazolo[3,2-a]azepane Derivatives from d-Hexoses

Delphine Marek* , Anne Wadouachi, Daniel Beaupère
  • *Laboratoire de Chimie Organique, Université de Picardie Jules Verne, 33 rue Saint-Leu F-80039 Amiens, France; Fax +33(03)22 82 75 62; E-mail: daniel.Beaupère@sc.u-picardie.fr
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Publication Date:
31 December 1999 (online)

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Reaction of cysteamine with protected d-hexoses yielded the corresponding thiazolidines. The thiazolidine derived from 2,3; 5,6-di-O-isopropylidene-d-mannofuranose was obtained stereoselectively and a subsequent N-heterocyclisation led to a diastereomerically pure analogue of pyrrolizidine. Alternatively, a "one-pot" procedure for synthesis of pure [1,3]thiazolo[3,2-a]azepane derivatives was realized from 6-O-sulfonyl-d-hexoses.

2-aminoethanethiol - 6-O-sulfonyl-d-hexoses - N-heterocyclisation - [1,3]thiazolo[3,2-a]azepane - stereoselectivity