Atroposelective Synthesis of N-Arylindoles via Enantioselective N–H Bond Insertion

• DOI: 10.1021/acs.orglett.2c03003
• Publication Date: 2022-10-03T16:23:04Z
• Authors: Chao Niu; Yi Zhou; Qiang Chen; Yan Zhu; Shengbiao Tang; Zhi-Xiang Yu; Jiangtao Sun
• Keywords: 01 natural sciences; 0104 chemical sciences

We present here a rhodium-catalyzed asymmetric N-H insertion reaction, which is a concerted process revealed by DFT calculations, for the synthesis of novel axially chiral N-arylindoles by the reaction between indoles and diazonaphthoquinones. The reaction occurs at the N1 rather than C2/C3 positions of indoles, providing the chiral N-arylindoles in good yields and excellent enantiomeric ratios. Furthermore, this protocol is also amenable to the synthesis of chiral N-arylcarbazoles with excellent enantiocontrol.