Oxidative α-Trichloromethylation of Tertiary Amines: An Entry to α-Amino Acid Esters

alpha-Trichloromethylation of tertiary amines with trimethyl(trichloromethyl)silane by oxidative coupling, using DDQ as an oxidant, has been realized. The reaction is instantaneous, is scalable, and tolerates a broad range of functional groups and heteroarenes. The trichloromethylated products can be easily converted into beta,beta-dichloroamines, enamines, and alpha-amino acid esters under operationally simple conditions. This methodology provides an efficient alternative to the poisonous cyanation reactions for the synthesis of carboxylic acid and their derivatives.