Synthesis of oxindoles bearing a stereogenic 3-fluorinated carbon center from 3-fluorooxindoles.

Org Biomol Chem

School of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai, 201620, China.

Published: January 2022

3,3-Disubstituted oxindoles bearing a stereogenic 3-fluorinated carbon center are privileged structural motifs present in many bioactive molecules. The straightforward functionalization of 3-fluorooxindoles constitutes a powerful method for the synthesis of 3-fully substituted 3-fluorooxindoles, taking advantage of the ease of preparation of 3-fluorooxindoles with different substitution patterns and the atom efficiency of chemical reactions. In the past decade, many papers have appeared on the synthesis of 3-fully substituted 3-fluorooxindoles from 3-fluorooxindoles. Importantly, many asymmetric catalytic methods have been developed for the enantioselective synthesis of these valuable compounds. This review summarizes the achievements in this area, and overviews synthetic opportunities that still exist.

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http://dx.doi.org/10.1039/d1ob01964cDOI Listing

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