Synthesis and synthetic applications of α,β-dideuterio-α-amino esters promoted by samarium diiodide

A new, easy, and high-yielded route to isotopically labeled amino acid derivatives is reported. This process takes place through a SmI2-promoted 1,4-reduction of a variety of dehydroamino esters in the presence of D2O. The dideuterio amino esters were transformed into other dideuterated compounds such as alpha-amino acids and 1,2-amino alcohols. A mechanism to explain the 1,4-reduction process is also proposed.