Design and synthesis of optically active esters of γ-amino-β-oxo acids as precursors for the synthesis of tetramic acids derived from L-serine, L -tyrosine, and L-threonine

Matiadis, D; Igglessi-Markopoulou, O

dc.contributor.author	Matiadis, D	en
dc.contributor.author	Igglessi-Markopoulou, O	en
dc.date.accessioned	2014-03-01T01:59:40Z
dc.date.available	2014-03-01T01:59:40Z
dc.date.issued	2010	en
dc.identifier.issn	1434193X	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/29015
dc.subject	Acylation	en
dc.subject	Amino acids	en
dc.subject	Cyclization	en
dc.subject	Nitrogen heterocycles	en
dc.title	Design and synthesis of optically active esters of γ-amino-β-oxo acids as precursors for the synthesis of tetramic acids derived from L-serine, L -tyrosine, and L-threonine	en
heal.type	journalArticle	en
heal.identifier.primary	10.1002/ejoc.201000700	en
heal.identifier.secondary	http://dx.doi.org/10.1002/ejoc.201000700	en
heal.publicationDate	2010	en
heal.abstract	Tetramic acids bearing a hydroxyalkyl or hydroxybenzyl group at C-5 of the heterocyclic ring were successfully prepared. α-Amino acids appropriately protected and activated were used as acylating agents for the C-acylation of active methylene compounds. These novel synthesized intermediates, substituted γ-amino acids, were isolated in excellent yields and enantiomeric purities. Cyclization under basic conditions afforded the desired products in high yields and enantiomeric purity. An array of functionalized tetramic acids bearing a hydrophilic group on the side arm of the heterocyclic nucleus, as well as their intermediate β-hydroxy-γ-amino acids, were synthesized from suitably protected and activated L-serine, L-tyrosine, and L-threonine in two steps with good-to-excellent enantiomeric purities (up to 95%ee) and high yields (up to 92%). © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.	en
heal.journalName	European Journal of Organic Chemistry	en
dc.identifier.doi	10.1002/ejoc.201000700	en
dc.identifier.issue	31	en
dc.identifier.spage	5989	en
dc.identifier.epage	5995	en