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), 613-618. (doi:10.1039/c1nj20659a).
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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.
|Digital Object Identifier (DOI):||doi:10.1039/c1nj20659a|
|Subjects:||Q Science > QD Chemistry|
|Divisions:||Faculty of Natural and Environmental Sciences > Chemistry > Organic Chemistry: Synthesis, Catalysis and Flow
|Date Deposited:||15 Oct 2012 12:25|
|Last Modified:||27 Mar 2014 20:26|
|RDF:||RDF+N-Triples, RDF+N3, RDF+XML, Browse.|
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