Rh-Catalyzed Atroposelective Single-Carbon Insertion
Bowen Li, Valero G. Alfonso, Alessio Puggioli, Albert Solé‐Daura, Feliu Maseras, Marcos G. Suero
Abstract
High Resolution Image Download MS PowerPoint Slide Single-carbon insertion processes have gained considerable momentum over the past few years. Although innovative methods have emerged for converting indole or indene into quinoline or naphthalene cores, the enantioselective version of such ring-expansions to create (hetero)biaryl atropisomers has not been developed. Herein, we report the first enantioselective single-carbon insertion that converts 3-aryl indoles to atropochiral quinolines. Key in the process was the generation of a chiral Rh-carbynoid that mediated in the creation of the stereogenic C( sp 2 )–C( sp 2 ) axis.
Topics & Concepts
AtropisomerChemistryStereocenterEnantioselective synthesisIndeneIndole testNaphthaleneQuinolineArylInsertion reactionRing (chemistry)Carbon fibersCatalysisCombinatorial chemistryTetralinStereochemistryOrganic chemistryAlkylMaterials scienceComposite materialComposite numberAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and CatalysisMolecular spectroscopy and chirality