Asymmetric & alpha;-Allylation of N-Unprotected Amino Acid Esters with 1,3-Disubstituted Allyl Acetates Enabled by Chiral-Aldehyde/Palladium Catalysis

A chiral aldehyde/palladium catalysis-enabled asymmetric & alpha;-allylationof NH2-unprotected amino acid esters with 1,3-disubstitutedallyl acetates is described in this work. With the utilization ofdifferent chiral phosphine ligands, both the anti- and syn-selective allylation reactions are achievedenantioselectively. A series of & alpha;,& alpha;-disubstituted aminoacid esters bearing two adjacent chiral centers are produced in moderate-to-excellentyields, diastereoselectivities, and enantioselectivities.

Automated summary

This work describes a chiral aldehyde/palladium catalysis method for asymmetric α-allylation of NH2-unprotected amino acid esters with 1,3-disubstituted allyl acetates. Using different chiral phosphine ligands, both anti- and syn-selective allylation reactions are achieved enantioselectively. A series of α,α-disubstituted amino acid esters with two adjacent chiral centers are produced in moderate-to-excellent yields, diastereoselectivities, and enantioselectivities.