Highly Site- and Enantioselective Cu-Catalyzed Allylic Alkylation Reactions with Easily Accessible Vinylaluminum Reagents

Yunmi Lee, Katsuhiro Akiyama, Dennis G. Gillingham, M. Kevin Brown and Amir H. Hoveyda*

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

Y. Lee, K. Akiyama, D. G. Gillingham, M. Kevin Brown, A. H. Hoveyda, J. Am. Chem. Soc., 2008, 130, 446-447.

DOI: 10.1021/ja0782192

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Abstract

Vinylaluminum reagents prepared from the reaction of commercially available DIBAL-H and a terminal alkyne can be used directly without purification in catalytic asymmetric allylic alkylation reactions with allylic phosphates in the presence of a readily available chiral N-heterocyclic carbene (NHC) complex and a commercially available and air stable Cu salt.

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Synthesis of Quaternary Carbon Stereogenic Centers through Enantioselective Cu-Catalyzed Allylic Substitutions with Vinylaluminum Reagents

F. Gao. K. P. McGrath, Y. Lee, A. H. Hoveyda, J. Am. Chem. Soc., 2010, 132, 14315-14320.

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Key Words

1,4-dienes, DIBAL-H

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ID: J48-Y2008-0080