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

Angew Chem Int Ed Engl

Engineering Research Center of Coptis Development and Utilization, Ministry of Education, College of Pharmaceutical Sciences, Southwest University, 2 Tiansheng Road, 400715, Chongqing, P. R. China.

Published: May 2023

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.

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http://dx.doi.org/10.1002/anie.202301091DOI Listing

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