Synthesis 2015; 47(16): 2377-2384
DOI: 10.1055/s-0034-1380197
special topic
© Georg Thieme Verlag Stuttgart · New York

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
Further Information

Publication History

Received: 26 February 2015

Accepted: 12 March 2015

Publication Date:
02 April 2015 (online)

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.

Supporting Information

 
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