Asymmetric Dearomative Fluorination of 2‐Naphthols with a Dicarboxylate Phase‐Transfer Catalyst
Hiromichi Egami, Taiki Rouno, Tomoki Niwa, Kousuke Masuda, Kenji Yamashita, Yoshitaka Hamashima
Abstract
A linked dicarboxylate phase-transfer catalyst enables smooth asymmetric dearomative fluorination of 2-naphthols with Selectfluor under mild conditions to give the corresponding 1-fluoronaphthalenone derivatives in a highly enantioselective manner. This reaction, which is compatible with a range of functional groups, is the first example of catalytic asymmetric fluorination of 2-naphthols, and is expected to be useful in the synthesis of bioactive molecules.
Topics & Concepts
SelectfluorEnantioselective synthesisCatalysisChemistryPhase (matter)MoleculeCombinatorial chemistryOrganic chemistryStereochemistryFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis