Wang Lab Providing Direct Access to Enantioenriched 1,2-Alkylamino Alcohol Derivatives

The Wang Lab has developed a copper-catalyzed enantioselective synthesis of β-alkylamino lactones by an umpolung amination strategy using O-acylhydroxylamines as alkylamine precursors. This enantioselective amino lactonization reaction shows a broad substrate scope and high functional group tolerance, offering rapid entry to a wide array of β-alkylamino lactones in high efficiency and enantioselectivity from unsaturated carboxylic acids. Furthermore, an atom-economic one-component reaction from unsaturated O-acylhydroxylamines has also been achieved for the enantioselective formation of chiral 1,2-alkylamino lactones. This work also provides important mechanistic insights including critical role of noncovalent interaction on this copper-catalyzed enantioselective transformation. Finally, synthetic applications of this method have been demonstrated as a rapid approach to access diverse β-functionalized alkylamines, such as β-alkylamino ether and diversely functionalized β-alkylamino alcohols. Learn about their research in a recent JACS article available here.