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