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)

Record type: Article

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.

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e-pub ahead of print date: 18 May 2010

Published date: 23 August 2010

Keywords: maleimides, michael addition, organocatalysis

Organisations: Chemistry

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Identifiers

Local EPrints ID: 347706

URI: http://eprints.soton.ac.uk/id/eprint/347706

DOI: doi:10.1002/chem.201000239

ISSN: 0947-6539

PURE UUID: 455a2de1-9763-40a3-9d54-d29535a28a5d

ORCID for Ramon Rios:

orcid.org/0000-0002-3843-8521

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Date deposited: 29 Jan 2013 11:43

Last modified: 14 Mar 2024 12:51

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Contributors

Author: Andrea-Nekane R. Alba

Author: Guillem Valero

Author: Teresa Calbet

Author: Mercé Font-Bardía

Author: Albert Moyano

Author: Ramon Rios

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