Electrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and Hydroxy-Functionalized O-Heterocycles

Abstract

A convenient electrochemical oxidative cascade cyclization of alkenes equipped with pendant alcohols with general nucleophiles was developed. Using readily available diarylmethanimine and carboxylic acids as nucleophilic sources, a broad range of internal alkene and terminal alkene substrates could produce RCO₂- and Ar₂CN-functionalized O-heterocycles in moderate to high yields without the requirement for external oxidants and metals. These resulting products can subsequently be hydrolyzed to yield valuable NH₂- and OH-functionalized tetrahydrofurans and tetrahydropyranes under mild conditions. Importantly, the efficient conversion of secondary alcohol products to amines with complete inversion of configuration enhances the methodology, enabling the construction of 2-aryl-3-amino tetrahydrofuran with high and complementary diastereoselectivity.