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3-Aminoacetylthiazolidine-4-carboxylate esters and their l-thia-4-azaspiro[4.5]decane-3-carboxylate derivatives. Synthesis and stereochemical properties

✍ Scribed by N. Pellegrini; B. Refouvelet; J.-C. Rouland; J.-F. Robert; B. Bachet

Publisher: Journal of Heterocyclic Chemistry
Year: 1997
Tongue: English
Weight: 481 KB
Volume: 34
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570340607

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✦ Synopsis

Abstract

Dimethyl thiazolidine‐2,4‐dicarboxylate 2 and ethyl l‐thia‐4‐azaspiro[4.5]decane‐3‐carboxylates 3‐5 were obtained as a diastereoisomeric mixture while their 3‐aminoacetyl derivatives were isolated in only one isomeric form. These reactions of N‐acylation were stereoselective, which can be explained by an interconversion of the diastereoisomers via a seco intermediate. The ^1^H nmr analysis of amides 6 and 11 exhibited the presence of both cis and trans amide bond conformations, whereas only one cis conformation was observed for spiro amides 8‐10 and 13‐15.

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