Electrochemical oxidative heterodifunctionalization of dehydroalanine: access to unnatural α,α-disubstituted amino esters

Abstract

A general, efficient, and mild Dha electrochemical modification strategy is reported, which enables a divergent route to various α,α-disubstituted amino esters via anodic cascade oxidation and nucleophilic attack. Depending on different nucleophilic reagents, dialkoxylation, diazidation, oxyselenation and oxythiolation can be achieved by this protocol under mild conditions, obviating the use of transition metals and external oxidants. Gram-scale synthesis and late-stage modifications of highly complex natural products showed the potential of this protocol in pharmaceutical research as well as other areas.