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Anion effect on enantioselective oxidative NHC catalysis: highly efficient kinetic resolution of tertiary alcohols and beyond

Organic Chemistry Frontiers, ISSN: 2052-4129, Vol: 10, Issue: 2, Page: 416-421
2022
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The effect of the counter-anion on enantio-control in oxidative NHC catalysis is demonstrated systematically for the first time. For kinetic resolution of oxindole-derived tertiary alcohols through NHC-catalyzed esterification, the identity of anions, either in the form of an additive or as the counter-anion in the azolium pre-catalyst, showed a significant effect on the enantioselectivity of the catalytic system. With the suitable choice of anions, highly efficient kinetic resolution (with k between 30 and >200) was achieved for a wide range of oxindole-derived tertiary alcohols bearing alkyl, aryl and functionalized substituents. The anion effect on other oxidative NHC-catalyzed processes such as formal cycloaddition is also demonstrated.

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