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

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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