Unprecedented directed oxidative cross-coupling of sulfahydantoins with aldehydesvia a radical sulfonate–sulfinate conversion

Abstract

An unexpected C–C cross-coupling radical oxidation involving aldehydes and glycine enolate equivalents such as activated mesyl-sulfahydantoins leading to β,β′-disubstituted aspartate semialdehydes (ASA) instead of the expected threonine analogues was observed and various α-substituted non-proteinogenic amino acid analogues were synthesized. A radical mechanism was envisaged and supported by DFT calculations.