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

Overview

Journal Synthesis (Stuttg)

Publisher Thieme

Specialty Chemistry

Date 2016 Jan 12

PMID 26752794

Citations 1

Authors

Arne R Philipps

Lars Fritze

Nico Erdmann

Dieter Enders

Affiliations

Soon will be listed here.

Abstract

An organocatalytic quadruple cascade initiated by a Friedel-Crafts-type reaction is described. The ()-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.

Citing Articles

New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems.

Curti C, Battistini L, Sartori A, Zanardi F Chem Rev. 2020; 120(5):2448-2612.

PMID: 32040305 PMC: 7993750. DOI: 10.1021/acs.chemrev.9b00481.

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