Synthesis of axially chiral amino acid derivatives via the selective monoesterification of 1,1′-biaryl-2,2′-dicarboxylic acids

Article abstract of DOI:10.1055/s-0032-1318506

Axially chiral amino acid derivatives were synthesized via a selective single-step monoesterification of 1,1′-binaphthyl-2,2′-dicarboxylic acids. In the presence of Ag₂CO₃, the alkylative monoesterification of a 1,1′-binaphthyl-2,2′-dicarboxylic acid with an alkyl halide proceeded selectively in a single operation. Curtius rearrangement of the monomethyl ester and successive alcoholysis of the corresponding isocyanate afforded the N-protected binaphthyl amino acids. Georg Thieme Verlag Stuttgart, New York.