Desilylation-Activated Propargylic Transformation: Enantioselective Copper-Catalyzed [3+2] Cycloaddition of Propargylic Esters with -Naphthol or Phenol Derivatives

摘要

A copper-catalyzed asymmetric [3+2] cycloaddition of 3-trimethylsilylpropargylic esters with either -naphthols or electron-rich phenols has been realized and proceeds by a desilylation-activated process. Under the catalysis of Cu(OAc)(2)H2O in combination with a structurally optimized ketimine P,N,N-ligand, a wide range of optically active 1,2-dihydronaphtho[2,1-b]furans or 2,3-dihydrobenzofurans were obtained in good yields and with high enantioselectivities (up to 96% ee). This represents the first desilylation-activated catalytic asymmetric propargylic transformation.