Synthesis of N-Urethane-protected gamma-amino-functionalized butenoates and tautomeric studies by means of NMR, X-ray crystallography and ab initio calculations

Detsi, A; Gavrielatos, E; Adam, MA; Igglessi-Markopoulou, O; Markopoulos, J; Theologitis, M; Reis, H; Papadopoulos, M

dc.contributor.author	Detsi, A	en
dc.contributor.author	Gavrielatos, E	en
dc.contributor.author	Adam, MA	en
dc.contributor.author	Igglessi-Markopoulou, O	en
dc.contributor.author	Markopoulos, J	en
dc.contributor.author	Theologitis, M	en
dc.contributor.author	Reis, H	en
dc.contributor.author	Papadopoulos, M	en
dc.date.accessioned	2014-03-01T01:51:21Z
dc.date.available	2014-03-01T01:51:21Z
dc.date.issued	2001	en
dc.identifier.issn	1434-193X	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/26270
dc.subject	C-acylation reactions	en
dc.subject	gamma-amino-alpha-cyano-beta-hydroxybutenoates tautomeric studies	en
dc.subject.classification	Chemistry, Organic	en
dc.subject.other	ACTIVE METHYLENE-COMPOUNDS	en
dc.subject.other	HYDROXYSUCCINIMIDE ESTERS	en
dc.subject.other	ENOL-TAUTOMERISM	en
dc.subject.other	TETRAMIC ACIDS	en
dc.subject.other	SPECTROSCOPY	en
dc.subject.other	INHIBITORS	en
dc.subject.other	PEPTIDES	en
dc.subject.other	AM1	en
dc.title	Synthesis of N-Urethane-protected gamma-amino-functionalized butenoates and tautomeric studies by means of NMR, X-ray crystallography and ab initio calculations	en
heal.type	journalArticle	en
heal.language	English	en
heal.publicationDate	2001	en
heal.abstract	N-Urethane-protected gamma -amino-alpha -cyano-beta -hydroxybutenoates were synthesized as potential statine analogues and the stability of their possible tautomers was assessed using NMR, X-ray crystallography and ab initio calculations. The results establish that the cis-enol tautomeric form is the most stable one both in solution (CDCl3) and in the solid phase. In full agreement with the experimental data, the theoretical calculations predicted that the cis-enol tautomer would be the minimum energy tautomer.	en
heal.publisher	WILEY-V C H VERLAG GMBH	en
heal.journalName	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY	en
dc.identifier.isi	ISI:000172277200018	en
dc.identifier.issue	22	en
dc.identifier.spage	4337	en
dc.identifier.epage	4342	en