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

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 stereogeni...

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Autores principales: Philipps, Arne R., Fritze, Lars, Erdmann, Nico, Enders, Dieter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4702351/
https://www.ncbi.nlm.nih.gov/pubmed/26752794
http://dx.doi.org/10.1055/s-0034-1380197
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author Philipps, Arne R.
Fritze, Lars
Erdmann, Nico
Enders, Dieter
author_facet Philipps, Arne R.
Fritze, Lars
Erdmann, Nico
Enders, Dieter
author_sort Philipps, Arne R.
collection PubMed
description 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.
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spelling pubmed-47023512016-01-06 An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel–Crafts/Michael/Michael/Aldol Condensation Sequence Philipps, Arne R. Fritze, Lars Erdmann, Nico Enders, Dieter Synthesis (Stuttg) Article 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. 2015-04-02 /pmc/articles/PMC4702351/ /pubmed/26752794 http://dx.doi.org/10.1055/s-0034-1380197 Text en License terms: CC BY-NC-ND (http://creativecommons.org/licenses/by-nc-nd/4.0/)
spellingShingle Article
Philipps, Arne R.
Fritze, Lars
Erdmann, Nico
Enders, Dieter
An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel–Crafts/Michael/Michael/Aldol Condensation Sequence
title An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel–Crafts/Michael/Michael/Aldol Condensation Sequence
title_full An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel–Crafts/Michael/Michael/Aldol Condensation Sequence
title_fullStr An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel–Crafts/Michael/Michael/Aldol Condensation Sequence
title_full_unstemmed An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel–Crafts/Michael/Michael/Aldol Condensation Sequence
title_short An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel–Crafts/Michael/Michael/Aldol Condensation Sequence
title_sort asymmetric organocatalytic quadruple domino reaction employing a vinylogous friedel–crafts/michael/michael/aldol condensation sequence
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4702351/
https://www.ncbi.nlm.nih.gov/pubmed/26752794
http://dx.doi.org/10.1055/s-0034-1380197
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