Synthesis of Axially Chiral Amino Acid Derivatives via the Selective Monoesterification of 1,1′-Biaryl-2,2′-dicarboxylic Acids

Abstract

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.

Key words

unnatural amino acid - monoesterification - half-ester - biaryl - axial chirality

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