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

doi:10.1055/s-0031-1289683

PAPER

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;

Abstract

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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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References

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