Intercepted decarboxylative allylations of nitroalkanoates

Meghan Schmitt, Alexander J. Grenning, Jon A. Tunge

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

Using palladium-catalyzed decarboxylation, several cascade reactions of allyl and prenyl nitroalkanoates that lead to nitro-containing chemical building blocks are described. A nitronate Michael addition/Tsuji-Trost allylation cascade was developed, leading to functionally dense chemical building blocks. Likewise, a Tsuji-Trost/decarboxylative protonation sequence was developed for the synthesis of orthogonally functionalized 2° nitroalkanes. The latter method provides rapid access to the indolizidine core.

Original languageEnglish (US)
Pages (from-to)4494-4497
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number34
DOIs
StatePublished - Aug 22 2012
Externally publishedYes

Keywords

  • Decarboxylative coupling
  • Indolizidine alkaloids
  • Multi-component reactions
  • Pd-catalysis
  • Tsuji-Trost allylation

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