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Synthesis 2012(5): 773-782  
DOI: 10.1055/s-0031-1289683
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of Functionalized Chromans via a One-Pot Organocatalytic Domino Michael-Hemiacetalization or -Lactonization and Dehydration Sequence

Dieter Enders*, Gregor Urbanietz, Robert Hahn, 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 20 December 2011
Publication Date:
30 January 2012 (online)

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Abstract

Starting from 2-(nitrovinyl)phenols and various cyclic dicarbonyl nucleophiles, a one-pot thiourea-catalyzed diastereo- and enantioselective synthesis of polyfunctionalized chroman derivatives via a domino Michael-hemiacetalization and dehydration sequence as well as via a domino Michael-lactonization reaction is reported. Cyclopenta[b]chromenes, tricyclic spirochromans, and tetrahydro-1H-xanthenes bearing a variety of functional groups can be synthesized in this way in good to excellent yields (56-91%) and with very good diastereo- (88-99% de) and enantioselectivities (83-99% ee).

Key words

organocatalysis - domino reaction - thiourea - one-pot reaction - chromans

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CCDC 859260 contains the supplementary crystallographic data of 5d 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.