Phosphine-catalyzed γ-addition of nitroacetates to allenoates for enantioselective creation of α,α-disubstituted α-amino acid precursors

Enantioselective gamma-addition of readily available alpha-substituted nitroacetates to allenoates has been achieved. This protocol provides a straightforward asymmetric synthesis of optically enriched alpha,alpha-disubstituted alpha-amino acid precursors, a class of molecular architectures that are of great importance in biological sciences. In the presence of amino acid-derived phosphine catalysts, the gamma-addition proceeded efficiently, forming products containing a tetra-substituted stereogenic center in high yields with good to excellent enantioselectivities.

Automated summary

Enantioselective gamma-addition of readily available alpha-substituted nitroacetates to allenoates has been achieved, providing a straightforward asymmetric synthesis of optically enriched alpha,alpha-disubstituted alpha-amino acid precursors. The reaction proceeds efficiently with high yields and good to excellent enantioselectivities in the presence of amino acid-derived phosphine catalysts, forming products containing a tetra-substituted stereogenic center.