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Chem Rev. 2016 Mar 9;116(5):2937-81. doi: 10.1021/acs.chemrev.5b00381. Epub 2016 Feb 8.

Homologation Reaction of Ketones with Diazo Compounds.

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Department of Chemistry and Bioengineering, Tampere University of Technology , Korkeakoulunkatu 8, Tampere, FI-33101 Finland.
Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidad of Lisboa , Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal.


This review covers the addition of diazo compounds to ketones to afford homologated ketones, either in the presence or in the absence of promoters or catalysts. Reactions with diazoalkanes, aryldiazomethanes, trimethylsilyldiazomethane, α-diazo esters, and disubstituted diazo compounds are covered, commenting on the complex regiochemistry of the reaction and the nature of the catalysts and promoters. The recent reports on the enantioselective version of ketone homologation reactions are gathered in one section, followed by reports on the use of cyclic ketones ring expansion in total synthesis. Although the first reports of this reaction appeared in the literature almost one century ago, the recent achievements, in particular, for the asymmetric version, forecast the development of new breakthroughs in the synthetically valuable field of diazo chemistry.

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