Organic Letters
Organic Letters
5 years ago

Enantioselective Nickel-Catalyzed Mizoroki–Heck Cyclizations To Generate Quaternary Stereocenters

Enantioselective Nickel-Catalyzed Mizoroki–Heck Cyclizations To Generate Quaternary Stereocenters
Ling Wu, Bo Qu, Liana Hie, Xumu Zhang, Jinhua J. Song, Nizar Haddad, Neil K. Garg, Marisa C. Kozlowski, Carl A. Busacca, Jean-Nicolas Desrosiers, Chris H. Senanayake, Sergei Tcyrulnikov, Dmitry Kurouski, Jialin Wen, Nathan K. Yee, Nelu Grinberg, Soumik Biswas
The development of enantioselective carbon–carbon bond couplings catalyzed by nonprecious metals is highly desirable in terms of cost efficiency and sustainability. The first nickel-catalyzed enantioselective Mizoroki–Heck coupling is reported. This transformation is accomplished via mild reaction conditions, leveraging on QuinoxP* as a chiral ligand to afford oxindoles containing quaternary stereocenters. Good reactivity and selectivity are observed in the presence of various functional groups. Computational studies suggest that the oxidative addition assembles an atropisomeric intermediate responsible for the facial selectivity of the insertion step.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01054

DOI: 10.1021/acs.orglett.7b01054

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