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

Abstract

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 4-aryl-2-naphthols with a chiral tridentate oxovanadium(IV) complex furnished the corresponding 4,4′-biaryl-1,1′-binaphthols in good yields.

Key words

aryne - β-diketone - carbon–carbon bond insertion - 4-aryl-2-naphthol - BINOL

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