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Catalytic, Nucleophilic Allylation of Aldehydes with Allyl Acetate

Scott E. Denmark* and Son T. Nguyen

*Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, Email: sdenmarkillinois.edu

S. E. Denmark, S. T. Nguyen, Org. Lett., 2009, 11, 781-784.

DOI: 10.1021/ol8028725 (free Supporting Information)


Abstract

Under catalysis by ruthenium trichloride in the presence of carbon monoxide, water, and triethylamine, a wide range of aromatic, olefinic, and aliphatic aldehydes are efficiently allylated with allyl acetate under mild conditions. The stoichiometric byproducts of this reaction are carbon dioxide and acetic acid.

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Key Words

Homoallylic Alcohols


ID: J54-Y2009-0480