Catalytic α-Allylation of Unprotected Amino Acid Esters
Ping Fang, Mani Raj Chaulagain and Zachary D. Aron*
*Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States, Email: zaronindiana.edu
P. Fang, M. R. Chaulagian, Z. D. Aron, Org. Lett., 2012, 14, 2130-2133.
DOI: 10.1021/ol300665n (free Supporting Information)
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The use of catalytic loadings of picolinaldehyde and Ni(II) salts in catalytic α-allylation of unprotected amino acid esters induces preferential reactivity at the enolizable α-carbon over the free nitrogen with electrophilic palladium π-allyl complexes to produce α-quaternary α-allyl amino acid esters. Additionally, the use of chiral ligands to access enantioenriched α-quaternary amino acid esters from racemic precursors is demonstrated.
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