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Enantioselective addition of oxazolones to maleimides. An easy entry to quaternary aminoacids

Alba, Andrea-Nekane R., Valero, Guillem, Calbet, Teresa, Font-Bardía, Mercé, Moyano, Albert and Rios, Ramon (2012) Enantioselective addition of oxazolones to maleimides. An easy entry to quaternary aminoacids New Journal of Chemistry, 36, (3), pp. 613-618. (doi:10.1039/c1nj20659a).

Record type: Article

Abstract

The catalytic enantioselective addition of 2-tert-butyl-4-aryl-1,3-oxazol-5-ones to maleimides is reported. The addition takes place exclusively at the C-4 position of the oxazolone ring, giving access to quaternary amino acid derivatives. The reaction is catalyzed by readily available chiral bases such as (DHQD)2PYR, rendering the final compounds in good yields and with moderate to good diastereo- and enantioselectivities. When the C-4-substituent of the 2-tert-butyl-oxazolone is an alkyl group, the regioisomeric C-2 addition product is also obtained.



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e-pub ahead of print date: 28 November 2011
Published date: March 2012
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 344063
URI: http://eprints.soton.ac.uk/id/eprint/344063
ISSN: 1144-0546
PURE UUID: 2efcb7c8-448e-424d-b8b4-ad986587d4f0
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 15 Oct 2012 12:25
Last modified: 18 Jul 2017 05:20

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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 ORCID iD

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