Cu-Catalyzed Chemodivergent, Stereoselective Propargylic Dearomatization and Etherification of 2-Naphthols
Braja Gopal Das, Sadhna Shah, Arko Das, Vinod K. Singh
Abstract
The first stereoselective propargylic dearomatization of 2-naphthol derivatives is reported using a chiral CuII–L10 complex. The reaction shows chemodivergent reactivity and produced propargyl dearomatization and etherification product for differently substituted 2-naphthols. Both the reactions generate the desired products in high yields with excellent chemo- and stereoselectivities (up to 99% ee, dr = 9:1) by using only 2 mol % catalyst loading. Dearomatization products contain a contiguous all-carbon quaternary–tertiary stereocenter and a terminal alkyne functionality.
Topics & Concepts
StereocenterChemistryStereoselectivityPropargylAlkyneCatalysisReactivity (psychology)Organic chemistryMedicinal chemistryEnantioselective synthesisPathologyMedicineAlternative medicineCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions