Atroposelective Synthesis of Axially Chiral 4-Aryl α-Carbolines via <i>N</i>-Heterocyclic Carbene Catalysis
Rui Ma, Xiaoxue Wang, Qiaoyu Zhang, Lei Chen, Jian Gao, Jie Feng, Donghui Wei, Ding Du
Abstract
-heterocyclic carbene (NHC)-catalyzed atroposelective formal [3 + 3] annulation of 4-nitrophenyl 3-arylpropiolates with 2-sulfonamidoindolines. The synthetic utility of the title compounds has been demonstrated by the diverse late-stage structural modifications. Density functional theory calculations were also conducted to illuminate the key factors for controlling the origin of the enantioselectivity. This strategy not only provides an efficient pathway to access axially chiral α-carboline atropisomers but also offers a novel catalytic enantioselective mode for the construction of axially chiral heterobiaryls by using NHC-bound alkynyl acylazoliums.
Topics & Concepts
AtropisomerCarbeneChemistryAnnulationAxial symmetryEnantioselective synthesisCatalysisArylAxial chiralityCombinatorial chemistryDensity functional theoryStereochemistryComputational chemistryOrganic chemistryPhysicsQuantum mechanicsAlkylAxial and Atropisomeric Chirality SynthesisAlgebraic structures and combinatorial modelsMolecular spectroscopy and chirality