Journal
ORGANIC LETTERS
Volume 14, Issue 8, Pages 2130-2133Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol300665n
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- Indiana University
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Catalytic alpha-allylation of unprotected amino acid esters to produce alpha-quaternary alpha-allyl amino acid esters is reported. Catalytic loadings of picolinaldehyde and Ni(II) salts induce preferential reactivity at the enolizable alpha-carbon of amino acid esters over the free nitrogen with electrophilic palladium pi-allyl complexes. Fourteen examples are given. Additionally, the use of chiral ligands to access enantioenriched alpha-quaternary amino acid esters from racemic precursors is demonstrated by the enantioselective synthesis of alpha-allyl phenylalanine methyl ester from racemic phenylalanine methyl ester.
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