Rapid decarboxylative allylation of nitroalkanes

Alexander J. Grenning, Jon A. Tunge

Research output: Contribution to journalArticlepeer-review

51 Scopus citations

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/ Dials-Alder sequences allows the facile synthesis of relatively complex substrates that undergo diastereoselectlve decarboxylatlve allylatlon.

Original languageEnglish (US)
Pages (from-to)740-742
Number of pages3
JournalOrganic Letters
Volume12
Issue number4
DOIs
StatePublished - Feb 19 2010
Externally publishedYes

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