Cobalt-Catalyzed Asymmetric Deuteration of α-Amidoacrylates for Stereoselective Synthesis of α,β-Dideuterated α-Amino Acids

Abstract

A cobalt-catalyzed deuteration of amidoacrylates using deuterated methanol afforded α,β-dideuterio-α-amino esters in excellent enantiomeric ratios (mostly >95 : 5) and almost complete deuteration (99 %). The new protocol was used to prepare dideuterio-α-amino acid fragments in some drugs. Furthermore, the stereoselective deuteration was applied in a concise synthesis of dideuterio l-DOPA.

Keywords: Amidoacrylates; Amino Acids; Asymmetric Hydrogenation; Cobalt Catalysis; Deuteration.