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Synthesis 2015; 47(16): 2377-2384
DOI: 10.1055/s-0034-1380197
DOI: 10.1055/s-0034-1380197
special topic
An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel–Crafts/Michael/Michael/Aldol Condensation Sequence
Weitere Informationen
Publikationsverlauf
Received: 26. Februar 2015
Accepted: 12. März 2015
Publikationsdatum:
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.
Key words
organocatalysis - domino reaction - quadruple cascade - asymmetric catalysis - alkenylationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380197.
- Supporting Information
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