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 (2011) 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).

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Description/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.



Item Type: Article
Digital Object Identifier (DOI): doi:10.1039/c1nj20659a
ISSNs: 1144-0546 (print)
Subjects: Q Science > QD Chemistry
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow
ePrint ID: 344063
Date :
Date Event
28 November 2011e-pub ahead of print
March 2012Published
Date Deposited: 15 Oct 2012 12:25
Last Modified: 17 Apr 2017 16:31
Further Information:Google Scholar
URI: http://eprints.soton.ac.uk/id/eprint/344063

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