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Mild and Tunable Benzoic Acid Catalysts for Rearrangement Reactions of Allylic Alcohols

J. Adam McCubbin*, Samantha Voth and Oleg V. Krokhin

*Department of Chemistry, University of Winnipeg, 515 Portage Avenue, Winnipeg, MB R3B 2E9, Canada, Email: a.mccubbinuwinnipeg.ca

J. A. McCubbin, S. Voth, O. V. Krokhin, J. Org. Chem., 2011, 76, 8537-8542.

DOI: 10.1021/jo201540p (free Supporting Information)


Abstract

Commercially available and very inexpensive benzoic acids catalyze an efficient and simple isomerization of readily prepared allylic alcohols to yield cyclic products, unusual enyne, and dienols. The catalysts can be tuned for reactivity and substrate sensitivity.

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Key Words

Allylic Alcohols, Isomerizations, Organocatalysis


ID: J42-Y2011-3130