Journal of Heterocyclic Chemistry p. 1685 - 1691 (1997)
Update date:2022-08-03
Topics:
Pellegrini
Refouvelet
Dachet
Rouland
Robert
Dimethyl thiazolidine-2,4-dicarboxylate 2 and ethyl 1-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 1H nmr analysis of amides 6 and 11 exhibited the presence of both cis and irons amide bond conformations, whereas only one cis conformation was observed for spiro amides 8-10 and 13-15.
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