An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel–Crafts/Michael/Michael/Aldol Condensation Sequence

Arne R. Philipps; Lars Fritze; Nico Erdmann; Dieter Enders

doi:10.1055/s-0034-1380197

Synthesis, Table of Contents

Synthesis 2015; 47(16): 2377-2384
DOI: 10.1055/s-0034-1380197

special topic

An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel–Crafts/Michael/Michael/Aldol Condensation Sequence

Arne R. Philipps

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: enders@rwth-aachen.de

,

Lars Fritze

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: enders@rwth-aachen.de

,

Nico Erdmann

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: enders@rwth-aachen.de

,

Dieter Enders*

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: enders@rwth-aachen.de

› Author Affiliations

Abstract

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Abstract

An organocatalytic quadruple cascade initiated by a Friedel–Crafts-type reaction is described. The (S)-diphenylprolinol trimethylsilyl ether catalyzed reaction yields highly functionalized cyclohexenecarbaldehydes bearing a 1,1-bis[4-(dialkylamino)phenyl]ethene moiety and three contiguous stereogenic centers. The reaction tolerates various functional groups and all products are obtained with very good diastereoselectivity and with virtually complete enantiomeric excess.

Key words

organocatalysis - domino reaction - quadruple cascade - asymmetric catalysis - alkenylation

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References

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