Stereoselective Synthesis of (Z)-Allyl Alcohols through Coinage-Metal-Catalyzed Nucleophilic Addition of Benzo[d]isoxazoles with Unactivated Propargyl Alcohols

Abstract

The Au/Ag-cocatalyzed stereoselective addition reaction of cyanophenol anion species generated in situ with unactivated propargyl alcohols to produce functionalized (Z)-allyl alcohols in mostly good yields is reported. Benzo[d]isoxazoles were found to be excellent building blocks for the production of highly reactive cyanophenol anions from Kemp elimination reactions, thus serving as a masked benzonitrile source for the preparation of organonitrile derivatives. Silver salt combined with gold catalyst were found to be necessary for the success of this transformation.