Chiral Anion Phase-Transfer Catalysis Applied to the Direct Enantioselective Fluorinative Dearomatization of Phenols

Chiral anion phase-transfer catalysis has enabled the
direct and
highly enantioselective fluorinative dearomatization of phenols catalyzed
by a BINOL-derived phosphate. The process efficiently transforms simple,
readily available phenols into fluorinated chiral small molecules
bearing reactive functionality under ambient reaction conditions with
high enantioselectivity. The close relationship of the products with
well-studied o-quinols provides numerous avenues
for synthetic elaboration and exciting opportunities for bioisosteric
replacement of hydroxyl with fluorine in natural products.