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Rapid decarboxylative allylation of nitroalkanes
Grenning, Alexander J. Tunge, Jon A.
Grenning, Alexander J.
Tunge, Jon A.
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Abstract
Allyl nitroacetates undergo decarboxylative allylation to provide tertiary nitroalkanes in high yield. Moreover, the transformations are complete within several minutes under ambient conditions. High yields result because O-allylation of the intermediate nitronates, which is typically problematic, is reversible under conditions of the decarboxylative allylation process. Lastly, 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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2010-02-19
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American Chemical Society
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Grenning_2010.pdf
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Grenning, A. J., & Tunge, J. A. (2010). Rapid decarboxylative allylation of nitroalkanes. Organic Letters, 12(4), 740. http://doi.org/10.1021/ol902828p