Deacylative Allylation: Allylic Alkylation via Retro-Claisen Activation
Alexander J. Grenning and Jon A. Tunge*
*Department of Chemistry, The University of Kansas, 1251
Wescoe Hall Drive, Lawrence, Kansas 66045-7528, United States, Email: tunge
ku.edu
A. J. Grenning, J. A. Tunge, J. Am. Chem. Soc., 2011, 133, 14785-14794.
DOI: 10.1021/ja205717f
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Abstract
In the “deacylative allylation”, the coupling partners, ketone pronucleophiles and readily available allylic alcohols undergo in situ retro-Claisen activation to generate an allylic acetate and a carbanion. In the presence of palladium, these reactive intermediates undergo catalytic coupling to form a new C-C bond.
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Key Words
Allylation, Carbonyl Compounds, Nitriles
ID: J48-Y2011-2720
