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

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 c...

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Published inOrganic letters Vol. 19; no. 13; pp. 3338 - 3341
Main Authors Desrosiers, Jean-Nicolas, Wen, Jialin, Tcyrulnikov, Sergei, Biswas, Soumik, Qu, Bo, Hie, Liana, Kurouski, Dmitry, Wu, Ling, Grinberg, Nelu, Haddad, Nizar, Busacca, Carl A, Yee, Nathan K, Song, Jinhua J, Garg, Neil K, Zhang, Xumu, Kozlowski, Marisa C, Senanayake, Chris H
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.07.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CARBON CENTERS
ACTIVATION
ASYMMETRIC-SYNTHESIS
CROSS-COUPLINGS
LIGANDS
OLEFINS
INTRAMOLECULAR ARYLCYANATION
BOND
BROMIDES
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Summary: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.
Bibliography:NIH RePORTER
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01054