Rapid decarboxylative allylation of nitroalkanes

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Issue Date
2010-02-19Author
Grenning, Alexander J.
Tunge, Jon A.
Publisher
American Chemical Society
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
Metadata
Show full item recordAbstract
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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Citation
Grenning, A. J., & Tunge, J. A. (2010). Rapid decarboxylative allylation of nitroalkanes. Organic Letters, 12(4), 740. http://doi.org/10.1021/ol902828p
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