Organocatalytic Asymmetric Dearomatization Reaction for the Synthesis of Axial Chiral Allene-Derived Naphthalenones Bearing Quaternary Stereocenters
Alemayehu Gashaw Woldegiorgis, Zhao Han, Xufeng Lin
Abstract
The highly regio-, diastereo-, and enantioselective dearomatization reaction of 1-substituted 2-naphthols and β,γ-alkynyl-α-imino esters with complete atom economy is disclosed via chiral phosphoric acid catalysis. This protocol provides facile and efficient access to asymmetric construction of a broad range of axially chiral allene-derived naphthalenones bearing quaternary stereocenters in good yields with high diastereoselectivities and enantioselectivities.
Topics & Concepts
StereocenterAlleneChemistryEnantioselective synthesisCatalysisPhosphoric acidOrganocatalysisCombinatorial chemistryStereochemistryOrganic chemistryAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods