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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.

SUBMITTER: Philipps AR

PROVIDER: S-EPMC4702351 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature

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

Philipps Arne R AR Fritze Lars L Erdmann Nico N Enders Dieter D

Synthesis 20150401 16

An organocatalytic quadruple cascade initiated by a Friedel-Crafts-type reaction is described. The (<i>S</i>)-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. ...[more]

PMID: 26752794

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