Asymmetric Access of γ-Amino Acids and γ-Amino Phosphonic Acid Derivatives via Copper-Catalyzed Enantioselective and Regioselective Hydroamination

gamma-Aminobutyric acid is a major inhibitory neurotransmitter in the mammalian central nervous system that plays a substantial role in brain disorders. gamma-Amino phosphonic acid is a unique surrogate of both natural and unnatural gamma-amino acid. Because of their unique biological activity, gamma-amino acid and gamma-amino phosphonic acid derivatives have attracted considerable attention. However, an efficient and straightforward method for constructing chiral gamma-substituted-gamma-amino acid and gamma-amino phosphonic acid derivatives remains a long-standing challenge. Herein, a highly efficient, versatile, and universal Cu-catalyzed asymmetric hydroamination of cinnamyl esters, cinnamyl phosphonates, and cinnamyl phosphine oxides is presented for accessing gamma-amino acid and gamma-amino phosphonic acid derivatives in good yields with high levels of enantiocontrol and regioselectivity. [GRAPHICS]

Automated summary

In this study, a highly efficient, versatile, and universal method for synthesizing gamma-amino acid and gamma-amino phosphonic acid derivatives was developed. The method allows for good yields of chiral products with high levels of enantiocontrol and regioselectivity.