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Synthesis of Chiral β,β-Disubstituted Ketones via CuH-Catalyzed Coupling of Aryl Alkenes and 3-Aryl-2H-azirines.

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A CuH-catalyzed coupling of aryl alkenes with 3-aryl-2H-azirines has been developed to synthesize optically active β,β-disubstituted ketones. We propose that this protocol occurs through a sequence in which a chiral… Click to show full abstract

A CuH-catalyzed coupling of aryl alkenes with 3-aryl-2H-azirines has been developed to synthesize optically active β,β-disubstituted ketones. We propose that this protocol occurs through a sequence in which a chiral alkylcopper complex regioselectively attacks the N-C2 bonds of azirines to generate chiral β-aryl imines, which additionally afford ketones upon hydrolysis. This method provides a novel complementary approach for synthesizing chiral β,β-disubstituted ketones in good yields with high levels of enantioselectivity under mild conditions.

Keywords: disubstituted ketones; coupling aryl; cuh catalyzed; aryl alkenes; alkenes aryl; catalyzed coupling

Journal Title: Organic letters
Year Published: 2022

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