4.8 Article

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

Journal

ORGANIC LETTERS
Volume 25, Issue 31, Pages 5790-5794

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c02027

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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.
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.

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