Transition metal-catalyzed decarboxylative allylation and benzylation reactions

Jimmie D. Weaver, Antonio Recio, Alexander J. Grenning, Jon A. Tunge

Research output: Contribution to journalReview articlepeer-review

958 Scopus citations

Abstract

Studies conducted in the field of homogeneous catalysis of decarboxylative allylation and benzylation reactions are presented. Shimizu and Ishii utilized the regiospecificity of decarboxylative coupling to allylate an α-fluoro ketone that proceeds via a fluorinated enolate. Behenna and Stoltz and later Trost and co-workers demonstrated the ability to control the stereochemistry at the R-carbon via enantioselective decarboxylative allylation of enol carbonates. Trost et al. have circumvented the sluggish transformations of ester enolate derivatives by utilizing 2-acyl imidazoles as surrogates for ester enolates. company utilized DcA of a dienol carbonate in their synthesis of trospectomycin sulfate, an aminocyclitol antibiotic. In 2009, Recio and Tunge published an improved synthetic protocol for decarboxylative allylations of α-cyanoacetic esters.

Original languageEnglish (US)
Pages (from-to)1846-1913
Number of pages68
JournalChemical Reviews
Volume111
Issue number3
DOIs
StatePublished - Mar 9 2011
Externally publishedYes

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