Dehydrogenative Cross-Coupling Reaction between N-Aryl alpha-Amino Acid Esters and Phenols or Phenol Derivative for Synthesis of alpha-Aryl alpha-Amino Acid Esters

摘要

A novel dehydrogenative cross-coupling (DCC) reaction between N-arylglycine esters and phenols or 1,3,5-trimethoxybenzene was developed by copper catalysis using di-tert-butyl peroxide (DTBP) as an oxidant. Under optimized conditions, a range of N-arylglycine esters 1 underwent the DCC reaction smoothly with various phenols 2 or 1,3,5-trimethoxybenzene 4 to give desired alpha-aryl alpha -amino acid esters 3 or 5, respectively, with high ortho regioselectivities in a moderate to excellent yield. A possible mechanism involving aromatic electrophilic substitution is proposed.