Polarity-Reversed Addition of Enol Ethers to Imines under Visible Light: Redox-Neutral Access to Azide-Containing Amino Acids

Abstract

A three-component and polarity-reversed addition cascade with a glyoxylate-based imine, an enol ether, and TMSN3 was established for the construction of γ-azido amino acids under visible light. This transformation features mild and redox-neutral conditions, affording a series of amino esters with excellent chemoselectivity. Preliminary mechanistic studies revealed that the addition of an oxyalkyl radical to imine is likely the rate-determining step. The obtained azido-containing amino esters could be successfully converted to various valuable building blocks.