Strong and Confined Acids Catalyze Asymmetric Intramolecular Hydroarylations of Unactivated Olefins with Indoles
Pinglu Zhang, Nobuya Tsuji, Jie Ouyang, Benjamin List
Abstract
, electronically neutral olefins have been reported and invariably require transition metal catalysts. Here we show how an efficient and highly enantioselective catalytic asymmetric intramolecular hydroarylation of aliphatic and aromatic olefins with indoles can be realized using strong and confined IDPi Brønsted acid catalysts. This unprecedented transformation is enabled by tertiary carbocation formation and establishes quaternary stereogenic centers in excellent enantioselectivity and with a broad substrate scope that includes an aliphatic iodide, an azide, and an alkyl boronate, which can be further elaborated into bioactive molecules.
Topics & Concepts
ChemistryStereocenterIntramolecular forceEnantioselective synthesisCatalysisCarbocationBrønsted–Lowry acid–base theoryCombinatorial chemistryIodideOrganocatalysisOrganic chemistryCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis