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Cu-Catalyzed Asymmetric Allylic Alkylations of Aromatic and Aliphatic Phosphates with Alkylzinc Reagents. An Effective Method for Enantioselective Synthesis of Tertiary and Quaternary Carbons

Monica A. Kacprzynski and Amir H. Hoveyda*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, Email: amir.hoveydabc.edu

M. A. Kacprzynski, A. H. Hoveyda, J. Am. Chem. Soc., 2004, 126, 10676-10681.

DOI: 10.1021/ja0478779


Abstract

Efficient enantioselective Cu-catalyzed alkylations of aromatic and aliphatic allylic phosphates bearing di- and trisubstituted olefins are promoted in the presence of a readily available chiral amino acid-based ligand. Tertiary and quaternary stereogenic carbon centers are delivered regioselectively in high ee.

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Key Words

Allylic Substitutions


ID: J48-Y2004-1690