3-AMINOACETYLTHIAZOLIDINE-4-CARBOXYLATE ESTERS AND THEIR 1-THIA-4-AZASPIRO[4.5]DECANE-3-CARBOXYLATE DERIVATIVES - SYNTHESIS AND STEREOCHEMICAL PROPERTIES

Authors
PELLEGRINI N REFOUVELET B BACHET B ROULAND JC ROBERT JF
Citation
N. Pellegrini et al., 3-AMINOACETYLTHIAZOLIDINE-4-CARBOXYLATE ESTERS AND THEIR 1-THIA-4-AZASPIRO[4.5]DECANE-3-CARBOXYLATE DERIVATIVES - SYNTHESIS AND STEREOCHEMICAL PROPERTIES, Journal of heterocyclic chemistry, 34(6), 1997, pp. 1685-1691
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
34
Issue
6
Year of publication
1997
Pages
1685 - 1691
Database
ISI
SICI code
0022-152X(1997)34:6<1685:3EAT1>2.0.ZU;2-Q
Abstract
Dimethyl thiazolidine-2,4-dicarboxylate 2 and ethyl 1-thia-4-azaspiro[ 4.5]decane-3-carboxylates 3-5 were obtained as a diastereoisomeric mix ture while their 3-aminoacetyl derivatives were isolated in only one i someric form. These reactions of N-acylation were stereoselective, whi ch can be explained by an interconversion of the diastereoisomers via a seco intermediate. The H-1 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 .