Organocatalytic Enantioselective Regiodivergent C−H Bond Functionalization of 1‐Naphthols with 1‐Azadienes
Chen Zhang, Yuyu Cheng, Fushuai Li, Yepeng Luan, Pengfei Li, Wenjun Li
Abstract
Abstract An organocatalyst‐controlled site‐selectivity switchable enantioselective Friedel‐Crafts reaction of unprotected 1‐naphthols has been established for the first time via the conjugate addition of 1‐azadienes. By two chiral complementary squaramide and phosphoric acid, both ortho ‐ and para ‐selective Friedel‐Crafts alkylations of 1‐naphthols were independently achieved with high efficiency and enantioselectivity. With this strategy, a wide range of optically active triarylmethanes have been achieved in high yields with good to excellent enantioselectivities. magnified image
Topics & Concepts
ChemistryEnantioselective synthesisSquaramideFriedel–Crafts reactionPhosphoric acidOrganocatalysisConjugateSelectivityCombinatorial chemistryOrganic chemistryOptically activeCatalysisMathematical analysisMathematicsAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsSynthesis of Indole Derivatives