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

ABSTRACT: 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.

SUBMITTER: Desrosiers JN

PROVIDER: S-EPMC5634709 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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

Desrosiers Jean-Nicolas JN Wen Jialin J Tcyrulnikov Sergei S Biswas Soumik S Qu Bo B Hie Liana L Kurouski Dmitry D Wu Ling L Grinberg Nelu N Haddad Nizar N Busacca Carl A CA Yee Nathan K NK Song Jinhua J JJ Garg Neil K NK Zhang Xumu X Kozlowski Marisa C MC Senanayake Chris H CH

Organic letters 20170612 13

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. ...[more]

PMID: 28604006

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