Core Structure-Oriented Asymmetric α-Allenylic Alkylation of Amino Acid Esters Enabled by Chiral Aldehyde/Palladium Catalysis
Hao Zhang, Wei Wen, Ze-Xi Lu, Zhu‐Lian Wu, Tian Cai, Qi‐Xiang Guo
Abstract
Aiming at the reported chiral synthons leading to manzacidins A and D, here we report a highly efficient catalytic asymmetric α-allenylic alkylation reaction of NH 2 -unprotected amino acid esters that is promoted by combined chiral aldehyde/palladium catalysis. Fifty examples of unnatural α,α-disubstituted amino acid esters are reported with good-to-excellent yields and stereoselectivities. Based on this methodology, a key intermediate leading to manzacidin C and its other three stereoisomers is prepared accordingly.
Topics & Concepts
SynthonChemistryAldehydePalladiumAlkylationCatalysisTsuji–Trost reactionAmino acidOrganic chemistryCombinatorial chemistryEnantioselective synthesisBiochemistryAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry Methods