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Synthesis 2011(12): 1880-1886  
DOI: 10.1055/s-0030-1260059
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Organocatalytic Aryloxylation of β-Keto Esters

Kevin Greenawaya, Paolo Dambruosoa, Alessandro Ferralia, Andrew J. Hazelwoodb, Filippo Sladojevichc, Darren J. Dixon*c
a School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK
b GlaxoSmithKline, Pharmaceuticals R&D Facility, Gunnels Wood Road, Stevenage, Herts, SG1 2NY, UK
c Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK
e-Mail: Darren.Dixon@chem.ox.ac.uk;
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Publication History

Received 12 March 2011
Publication Date:
20 May 2011 (online)

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Abstract

An efficient enantioselective aryloxylation of cyclic β-keto esters with a selection of substituted o-quinones catalyzed by a bifunctional cinchona alkaloid derivative, giving entry to tricyclic dioxin adducts with high enantio- and diastereoselectivity, is described.

Key words

aryloxylation - quinones - β-keto ester - organocatalysis - dioxins

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