Asymmetric Domino Heck/Dearomatization Reaction of β-Naphthols to Construct Indole–Terpenoid Frameworks
Dong‐Chao Wang, Pengpeng Cheng, Tingting Yang, Panpan Wu, Gui‐Rong Qu, Hai‐Ming Guo
Abstract
A palladium-catalyzed enantioselective Heck cyclization/dearomatization cascade via capturing the cyclized Heck π-allylpalladium intermediate by β-naphthols is reported, which provides a new strategy for the construction of chiral indole-terpenoid frameworks. This method affords indole-functionalized β-naphthalenone compounds bearing an all-carbon-substituted quaternary chiral center in excellent yields (up to 92%) and enantioselectivities (up to 94% ee). In addition, the utility of this method is showcased by the gram-scale syntheses and diverse transformations of the dearomatized products.
Topics & Concepts
ChemistryIndole testEnantioselective synthesisQuaternary carbonDominoHeck reactionTerpenoidOrganic chemistryCatalysisCombinatorial chemistryCascade reactionPalladiumStereochemistryCatalytic C–H Functionalization MethodsAxial and Atropisomeric Chirality SynthesisChemical synthesis and alkaloids