4.5 Article

Enantioselective Synthesis of 4,4′-Biaryl-BINOLs from Arynes and β-Diketones

Journal

SYNTHESIS-STUTTGART
Volume 47, Issue 19, Pages 2937-2944

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1380452

Keywords

aryne; beta-diketone; carbon-carbon bond insertion; 4-aryl-2-naphthol; BINOL

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The reaction of 2-(trimethylsilyl) phenyl triflate with aroylacetones in the presence of CsF gave the corresponding 4-aryl-2-naphthols. Substituted triflates also reacted with aroylacetones to afford 4-aryl-2-naphthols regioselectively. The enantioselective oxidation of 4aryl-2-naphthols with a chiral tridentate oxovanadium(IV) complex furnished the corresponding 4,4'-biaryl-1,1'-binaphthols in good yields.

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