Chiral lithium binaphtholate for enantioselective amination of acyclic α-alkyl-β-keto esters: Application to the total synthesis of L-carbidopa

Article abstract of DOI:10.1016/j.tet.2017.08.015

A chiral lithium binaphtholate catalyzes the enantioselective amination of α-alkyl-β-keto esters with azodicarboxylates to produce optically active α,α-disubstituted α-amino acid derivatives in high yields and with good to high enantioselectivities. A stoichiometric amount of lithium hydroxide efficaciously improved both the reactivity and enantioselectivity of amination. The resulting aminated product is readily convertible to L-carbidopa.