An Improved gem-Dimethylcyclopropanation Procedure Using Triisopropylsulfoxonium Tetrafluoroborate

Autor:	Michael G. Edwards, Richard J. Paxton, Richard J. K. Taylor, David S. Pugh
Rok vydání:	2008
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Ketone Tetrafluoroborate chemistry Cyclopropanation Yield (chemistry) Reagent Organic Chemistry Dimethylformamide Alcohol Medicinal chemistry Sodium hydride
Zdroj:	Synlett. 2008:521-524
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-2008-1042761
Popis:	A new procedure for the cyclopropanation of α,β-unsaturated carbonyl compounds and related systems is described which employs triisopropylsulfoxonium tetrafluoroborate and sodium hydride in dimethylformamide. Using this reagent, a range of α,β-unsaturated ketones (and an ester and a vinyl nitro example) has been converted into the corresponding gem-dimethylcyclopropyl carbonyl compounds; in addition, a preliminary result is described in which an activated alcohol is converted directly into a gem-dimethylcyclopropyl ketone by a one-pot tandem oxidation-cyclopropanation sequence, albeit in low yield.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b479f381828531f76176032570763be8 https://doi.org/10.1055/s-2008-1042761 Zobrazit plný text záznamu