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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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Abstract

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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Key Words

Amino Acid Esters, Allylation, Tsuji-Trost Reaction


ID: J54-Y2012-1230