Synergistic Pd/Cu catalysis for stereoselective allylation of vinylethylene carbonates with glycine iminoesters: Enantioselective access to diverse trisubstituted allylic amino acid derivatives

We reported a synergistic Pd/Cu catalyzed enantioselective decarboxylative allylation of vinylethylene carbonates with glycine iminoesters, which provides facile access to non-proteinogenic diverse trisubstituted allylic amino acid derivatives in high yields, exclusive regioselectivities and excellent stereoselectivities. This reaction tolerates a wide range of & gamma; and & beta;-aryl substituted vinylethylene carbonates with either electron-donating or electronwithdrawing groups. Significantly, this method was proven to be sufficient in the gram scale synthesis of chiral trisubstituted allylic amino acid while retaining the enantioselectivity and geometric control.

Automated summary

A synergistic Pd/Cu catalyzed enantioselective decarboxylative allylation of vinylethylene carbonates with glycine iminoesters has been reported, providing access to diverse trisubstituted allylic amino acids in high yields, regioselectivities, and stereoselectivities. The reaction is tolerant to a wide range of & gamma; and & beta;-aryl substituted vinylethylene carbonates with various electron-donating or electron-withdrawing groups. Importantly, the method has been proven to be effective in gram-scale synthesis of chiral trisubstituted allylic amino acids with retention of enantioselectivity and geometric control.