Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Asymmetric Construction of 3,3-Disubstituted Oxindoles Bearing Vicinal Quaternary–Tertiary Carbon Stereocenters Catalyzed by a Chiral-at-Rhodium Complex

Asymmetric Construction of 3,3-Disubstituted Oxindoles Bearing Vicinal Quaternary–Tertiary Carbon Stereocenters Catalyzed by a Chiral-at-Rhodium Complex
Lei Gong, Zijun Zhou, Eric Meggers, Bowen Han, Huihua Lin, Jun Cai
A highly diastereo- and enantioselective synthesis of 3,3-disubstituted oxindoles bearing vicinal quaternary–tertiary carbon centers is enabled by a chiral-at-rhodium Lewis acid catalyst starting from isatin N-protected ketimines and 2-acyl imidazoles. The excellent results with 93–99% yields, diastereoselectivities of 43:1 to >200:1, and high enantioselectivities of 98.4 to >99% confirm the potential of bis-cyclometalated rhodium catalysts for the development of effective asymmetric transformations.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00793

DOI: 10.1021/acs.joc.7b00793

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