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

Detsi, A; Gavrielatos, E; Adam, M-A; 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, M-A	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	2014-03-01T01:17:13Z
dc.date.available	2014-03-01T01:17:13Z
dc.date.issued	2001	en
dc.identifier.issn	1434193X	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/14393
dc.subject	γ-Amino-α-cyano-β-hydroxybutenoates	en
dc.subject	C-Acylation reactions	en
dc.subject	Tautomeric studies	en
dc.subject.other	alpha amino acid	en
dc.subject.other	ethyl 4 [(tert butoxycarbonyl)methylamino] 2 cyano 3 hydroxy 2 butenoate	en
dc.subject.other	gamma amino alpha cyano beta hydroxybutenoate derivative	en
dc.subject.other	methyl 4 [(tert butoxycarbonyl)methylamino] 2 cyano 3 hydroxy 2 butenoate	en
dc.subject.other	unclassified drug	en
dc.subject.other	urethan derivative	en
dc.subject.other	article	en
dc.subject.other	chemical reaction	en
dc.subject.other	drug structure	en
dc.subject.other	drug synthesis	en
dc.subject.other	molecular stability	en
dc.subject.other	nuclear magnetic resonance spectroscopy	en
dc.subject.other	structure analysis	en
dc.subject.other	X ray crystallography	en
dc.title	Synthesis of N-urethane-protected γ-amino-functionalized butenoates and tautomeric studies by means of NMR, X-ray crystallography and ab initio calculations	en
heal.type	journalArticle	en
heal.identifier.primary	10.1002/1099-0690(200111)2001:22<4337::AID-EJOC4337>3.0.CO;2-S	en
heal.identifier.secondary	http://dx.doi.org/10.1002/1099-0690(200111)2001:22<4337::AID-EJOC4337>3.0.CO;2-S	en
heal.publicationDate	2001	en
heal.abstract	N-Urethane-protected γ-amino-α-cyano-β-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.journalName	European Journal of Organic Chemistry	en
dc.identifier.doi	10.1002/1099-0690(200111)2001:22<4337::AID-EJOC4337>3.0.CO;2-S	en
dc.identifier.issue	22	en
dc.identifier.spage	4337	en
dc.identifier.epage	4342	en