Cobalt‐Catalyzed Asymmetric Deuteration of α‐Amidoacrylates for Stereoselective Synthesis of α,β‐Dideuterated α‐Amino Acids
Aibo Li, Xinjian Song, Qiao Ren, Peiwang Bao, Xinyu Long, Fuli Huang, Lvjiang Yuan, Jianrong Steve Zhou, Xurong Qin
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.
Topics & Concepts
CobaltStereoselectivityCatalysisEnantioselective synthesisAmino acidChemistryCombinatorial chemistryStereochemistryOrganic chemistryBiochemistryChemical Reactions and IsotopesAsymmetric Hydrogenation and CatalysisChemical Synthesis and Analysis