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

α-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 β,β-dichloroamines,
enamines, and α-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.