Nickel-Catalyzed Asymmetric Cross-Electrophile <i>trans</i>-Aryl-Benzylation of α-Naphthyl Propargylic Alcohols
Zhiyang Lin, Weitao Hu, Linchuan Zhang, Chuan Wang
Abstract
Herein, we report a nickel-catalyzed asymmetric three-component trans -dicarbofunctionalization of β-substituted α-naphthyl propargylic alcohols using readily available aryl and benzyl halides as the coupling partners under reductive conditions. This cross-electrophile strategy enables the synthesis of various axially chiral allylic alcohols bearing a tetrasubstituted olefinic unit in complete regio- and E selectivity, as well as high enantiocontrol. Relying on the hydroxyl group as the functional handle, such structural motifs are successfully derivatized into diverse functional-group-rich axially chiral alkenes.
Topics & Concepts
ElectrophileArylChemistryAllylic rearrangementCatalysisSelectivityHalideEnantioselective synthesisKetoneNickelFunctional groupCombinatorial chemistryOrganic chemistryMedicinal chemistryAlkylPolymerAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and CatalysisAlkaloids: synthesis and pharmacology