title: Chiral anion phase-transfer catalysis applied to the direct enantioselective fluorinative dearomatization of phenols.
abstract: 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.
authors: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors: Robert J
authors: RJ
authors: Phipps
authors: F Dean
authors: FD
authors: Toste
mesh_terms: D000838:Anions / Q000737:chemistry; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000838:Anions; D006845:Hydrocarbons, Fluorinated; D010636:Phenols