Universität zu Köln

Eroeksuez, Serap, Neudoerfl, Joerg M. and Berkessel, Albrecht ORCID: 0000-0003-0470-7428 (2017). Kinetic Resolution of 5-Substituted Oxazinones with Bifunctional Chiral Base/Squaramide Organocatalysts. Synlett, 28 (11). S. 1278 - 1282. STUTTGART: GEORG THIEME VERLAG KG. ISSN 1437-2096

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Abstract

5-Substituted oxazinones provide N-protected beta(2)-amino acid esters upon alcoholytic ring opening. Thus far, this access to enantiopure beta(2)-amino acids has been restricted to the use of enzymes (hydrolases) as catalysts for the kinetic resolution of racemic 5-substituted oxazinones, and branched alkyl or ortho-substituted aryl groups on the substrate oxazinone's 5-position were typically not tolerated. We herein report that certain bifunctional chiral base/squaramide organocatalysts, in particular those derived from cis-1,2-diaminocyclohexane or 9-amino-9-epi-quinine, allow the first organocatalytic kinetic resolution of this 'difficult' class of oxazinone substrates, affording N-protected beta(2)-amino acid esters with selectivity factors up to 43.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Eroeksuez, Serap UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Berkessel, Albrecht UNSPECIFIED orcid.org/0000-0003-0470-7428 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-226178
DOI:	10.1055/s-0036-1588852
Journal or Publication Title:	Synlett
Volume:	28
Number:	11
Page Range:	S. 1278 - 1282
Date:	2017
Publisher:	GEORG THIEME VERLAG KG
Place of Publication:	STUTTGART
ISSN:	1437-2096
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language AZLACTONES Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/22617