Atroposelective Synthesis of <i>N</i>-Arylindoles via Enantioselective N–H Bond Insertion
Chao Niu, Yi Zhou, Qiang Chen, Yan Zhu, Shengbiao Tang, Zhi‐Xiang Yu, Jiangtao Sun
Abstract
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.
Topics & Concepts
ChemistryEnantioselective synthesisRhodiumCatalysisEnantiomerCombinatorial chemistryStereoisomerismStereochemistryOrganic chemistryAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralitySphingolipid Metabolism and Signaling