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Synthesis 2011(12): 1905-1911  
DOI: 10.1055/s-0030-1260017
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalytic Asymmetric Synthesis of Functionalized 4H-Chromenes via a One-Pot Domino Michael-Hemiacetalization and Dehydration Sequence

Dieter Enders*, Gregor Urbanietz, Gerhard Raabe
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: enders@rwth-aachen.de;
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Publication History

Received 11 March 2011
Publication Date:
21 April 2011 (online)

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Abstract

A one-pot thiourea-catalyzed enantioselective synthesis of polyfunctionalized 4H-chromenes via a domino Michael-hemiacetalization reaction and subsequent dehydration is reported. Starting from 2-nitrovinylphenols and β-keto esters, the new protocol affords the 4H-chromenes bearing a variety of functional groups with good to excellent yields (76-95%) and enantioselectivities ranging from 30-99% ee. Both enantiomers are available at will depending on the ephedrine or pseudoephedrine-based thiourea catalyst used.

Key words

organocatalysis - cascade reaction - thiourea - one-pot reaction - 4H-chromene

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CCDC 816422 (4a), 816423 (ent-4b), 816424 (4f) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.