Enantioselective Synthesis of C-N Axially Chiral N-Aryloxindoles by Asymmetric Rhodium-Catalyzed Dual C-H Activation

Abstract

The first enantioselective Satoh-Miura-type reaction is reported. A variety of C-N axially chiral N-aryloxindoles have been enantioselectively synthesized by an asymmetric rhodium-catalyzed dual C-H activation reaction of N-aryloxindoles and alkynes. High yields and enantioselectivities were obtained (up to 99 % yield and up to 99 % ee). To date, it is also the first example of the asymmetric synthesis of C-N axially chiral compounds by such a C-H activation strategy.

Keywords: C−H activation; alkynes; axial chirality; heterocycles; rhodium.