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Rapid decarboxylative allylation of nitroalkanes.

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.

SUBMITTER: Grenning AJ

PROVIDER: S-EPMC2821453 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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Rapid decarboxylative allylation of nitroalkanes.

Grenning Alexander J AJ Tunge Jon A JA

Organic letters 20100201 4

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 synthesi ...[more]

PMID: 20088536

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