TUTCRIS - Tampereen teknillinen yliopisto

TUTCRIS

Homologation Reaction of Ketones with Diazo Compounds

Tutkimustuotos: Katsausartikkelivertaisarvioitu

Yksityiskohdat

AlkuperäiskieliEnglanti
Sivut2937-2981
Sivumäärä45
JulkaisuChemical Reviews
Vuosikerta116
Numero5
DOI - pysyväislinkit
TilaJulkaistu - 2016
OKM-julkaisutyyppiA2 Katsausartikkeli

Tiivistelmä

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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