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. 2010 Feb 19;12(4):740-2.
doi: 10.1021/ol902828p.

Rapid decarboxylative allylation of nitroalkanes

Alexander J Grenning  1 , Jon A Tunge
Affiliations

Rapid decarboxylative allylation of nitroalkanes

Alexander J Grenning et al. Org Lett. .

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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