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Carbene-Catalyzed Enantioselective Atherton-Todd Reaction for Kinetic Resolution of 1,1'-Biaryl-2,2'-diols and
Xiuli Wu1, Sha Zhao1, Fengrui Che1
1State Key Laboratory of Green Pesticide; Center for R&D of Fine Chemicals of Guizhou University, Huaxi District, Guiyang 550025, China.
Abstract:
Enantiomerically pure 1,1'-bi-2,2'-naphthols (BINOLs) are indispensable scaffolds for asymmetric catalysis, functional materials, and bioactive molecules. Herein, we report an N-heterocyclic carbene-catalyzed asymmetric Atherton-Todd reaction that enables highly efficient kinetic resolution of BINOLs, affording enantioenriched phosphorylated derivatives with selectivity factors up to 492. In contrast to established acyl-transfer-based resolutions, this study establishes asymmetric phosphoryl transfer to achieve O-functionalization for BINOL resolution and highlights heteroatom-centered NHC catalysis as an underexplored paradigm in asymmetric synthesis.
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