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Synthesis 2010(4): 567-572  
DOI: 10.1055/s-0029-1217146
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Microwave-Assisted Organocatalytic Quadruple Domino Reactions of Acetaldehyde and Nitroalkenes

Dieter Enders*, Ralf Krüll, Wolfgang Bettray
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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Publikationsverlauf

Received 13 October 2009
Publikationsdatum:
27. November 2009 (online)

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Abstract

A microwave-assisted, organocatalytic domino Michael/Henry condensation/Michael/aldol condensation reaction has been developed. Employing acetaldehyde and nitroalkenes as substrates, this quadruple cascade allows an efficient asymmetric synthesis of trisubstituted cyclohexene carbaldehydes in moderate to good yields (25-45%) and high enantioselectivities (ee = 89 to >99%). ESI-MS measurements were carried out to support the proposed complex catalytic cycle.

Key words

organocatalysis - cascade reaction - Michael addition - aldol condensation - cyclohexene carbaldehydes

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