Highly Enantioselective Synthesis of γ-Carboxy-β-amino Acids via Desymmetric Alcoholysis of 3-Aminoglutaric Anhydrides

초록

A highly enantioselective synthetic method of gamma-carboxy-beta-amino acids has been developed via the desymmetric alcoholysis of 3-aminoglutaric anhydrides. The asymmetric desymmetrization of N-trifluoroacetyl-N-acyl-3-aminoglutaric anhydrides with alcohols in the presence of bis-quinine-squaramide as a bifunctional organocatalyst afforded gamma-carboxy-beta-amino acids with up to 99% yield and 98% ee. These versatile compounds can be readily converted into various chiral derivatives. The practicality of this method was further demonstrated by its successful application in the synthesis of beta-amino acid and beta-amino lactone derivatives.

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