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Rapid Decarboxylative Allylation of Nitroalkanes

Alexander J. Grenning and Jon A. Tunge*

*Department of Chemistry, The University of Kansas, Lawrence, Kansas 66045, Email: tungeku.edu

A. J. Grenning, J.A. Tunge, Org. Lett., 2010, 12, 740-742.

DOI: 10.1021/ol902828p


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Abstract

Allyl nitroacetates undergo decarboxylative allylation to provide tertiary nitroalkanes in high yield within several minutes under ambient conditions. The preparation of substrate allyl nitroacetates by tandem Knoevenagel/Diels-Alder sequences allows the facile synthesis of relatively complex substrates that undergo diastereoselective decarboxylative allylation.

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Key Words

Nitro Compounds, Allylation


ID: J54-Y2010-0400