Abstract
A new procedure for the cyclopropanation of alpha,beta-unsaturated carbonyl compounds and related systems is described which employs triisopropylsulfoxonium tetrafluoroborate and sodium hydride in dimethylformamide. Using this reagent, a range of alpha,beta-unsaturated ketones (and an ester and a vinyl nitro example) has been converted into the corresponding gem-dimethylcyclopropoyl carbonyl compounds; in addition, a preliminary result is described in which an activated alcohol is converted directly into a gem-dimethylyclopropyl ketone by a one-pot tandem oxidation-cyclopropanation sequence, albeit in low yield.
Original language | English |
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Pages (from-to) | 521-524 |
Number of pages | 4 |
Journal | Synlett |
Issue number | 4 |
DOIs | |
Publication status | Published - 3 Mar 2008 |
Keywords
- cyclopropanes
- cyclopropanation
- tandem oxidation procedures
- sulfoxonium salts
- ruthenium tetroxide
- TANDEM OXIDATION PROCESSES
- ALKYLIDENE TRANSFER REAGENTS
- ORGANIC-SYNTHESIS
- DIMETHYLSULFOXONIUM METHYLIDE
- FUNCTIONALIZED CYCLOPROPANES
- OXOSULFONIUM SALTS
- ALLYLIC ALCOHOLS
- ESTERS
- YLIDES