Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 37, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202207518
Keywords
Cyclization; Dearomatization; Enantioselectivity; Gold Catalysis; Metal-Ligand Cooperation
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Funding
- NSF [CHE 1800525, MRI-1920299]
- National Science Foundation [CNS-1725797]
- California NanoSystems Institute
- Materials Research Science and Engineering Center (MRSEC) at UC Santa Barbara [NSF DMR 1720256]
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A gold(I)-catalyzed enantioselective dearomatization is achieved through metal-chiral ligand cooperation. A new and divergent synthesis of chiral bifunctional binaphthyl-2-ylphosphines is developed for rapid access to these ligands, enabling broad substrate scope. The selective acceleration of one enantiomer formation is achieved through hydrogen bonding between substrate and ligand remote basic group, leading to enantiomeric excesses up to 98%.
A gold(I)-catalyzed enantioselective dearomatization is achieved via metal-chiral ligand cooperation. A new and divergent synthesis of chiral bifunctional binaphthyl-2-ylphosphines is developed to allow rapid access to these ligands, which in turn facilitate the application of this chemistry to a broad substrate scope including 1-naphthols, 2-naphthols, and phenols. Enantiomeric excesses up to 98 % are achieved via selective acceleration of one enantiomer formation enabled by hydrogen bonding between substrate and ligand remote basic group. DFT calculations lend support to the cooperative catalysis and substantiate the reaction stereochemical outcomes.
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