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Published on: May 26, 2019
Cu-Catalyzed Asymmetric Olefinative Conjugate Addition of Dialkylzinc Reagents
Piero Soppelsa1, Francesco Vaghi1, Giulia Licini1,2
1Department of Chemical Sciences, University of Padova, via Marzolo 1, 35131 Padova, Italy.
Abstract:
The asymmetric olefinative conjugate addition (AOCA) of dialkylzinc reagents is presented. This involves the Cu-catalyzed enantioselective conjugate addition of dialkylzinc reagents to α-phosphonyl acrylonitrile derivatives, which then allows for an olefinative quench with an aldehyde via Horner-Wadsworth-Emmons reaction. This one-pot sequence efficiently produces chiral internal olefins, addressing a common limitation of Cu-catalyzed enantioselective allylic substitutions, which typically only generate terminal alkenes. Various structurally diverse products are obtained with high yields, complete diastereocontrol, and an er of up to 98:2.
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