Enantioselective organocatalytic addition of azlactones to maleimides: a highly stereocontrolled entry to 2,2-disubstituted-2H-oxazol-5-ones


Alba, Andrea-Nekane R., Valero, Guillem, Calbet, Teresa, Font-Bardía, Mercé, Moyano, Albert and Rios, Ramon (2010) Enantioselective organocatalytic addition of azlactones to maleimides: a highly stereocontrolled entry to 2,2-disubstituted-2H-oxazol-5-ones. [in special issue: in honor of Professor Jose Barluenga for his 70th birthday] Chemistry - A European Journal, 16, (32), 9884-9889. (doi:10.1002/chem.201000239). (PMID:20486106).

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Description/Abstract

The first highly diastereo- and enantioselective organocatalytic synthesis of 2,2-disubstituted-2H-oxazol-5-ones is described. The addition of oxazolones to maleimides is promoted by bifunctional thiourea catalysts, which afford the corresponding 2,2-disubstituted-2H-oxazol-5-ones with total regio- and stereocontrol.

Item Type: Article
ISSNs: 0947-6539 (print)
1521-3765 (electronic)
Keywords: maleimides, michael addition, organocatalysis
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Natural and Environmental Sciences > Chemistry
ePrint ID: 347706
Date Deposited: 29 Jan 2013 11:43
Last Modified: 27 Mar 2014 20:29
URI: http://eprints.soton.ac.uk/id/eprint/347706

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