Synthesis of 3,3-Dialkyl-Substituted Isoindolinones Enabled by Nickel-Catalyzed Reductive Dicarbofunctionalization of Enamides.

Org Lett

Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China.

Published: July 2021

Herein we report the nickel-catalyzed reductive dicarbofunctionalization of 1,1-disubstituted enamides with unactivated alkyl iodides to access the 3,3-dialkyl-substituted isoindolinone frameworks. This tandem cyclization/reductive coupling protocol exhibits broad functional group tolerance under mild conditions. The utilization of commercially accessible chiral Bn-Biox ligand allows excellent enantioselectivities to forge the tetrasubstituted stereocenters.

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http://dx.doi.org/10.1021/acs.orglett.1c01871DOI Listing

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