1073-76-3Relevant articles and documents
Modulation of the reactivity profile of IBX by ligand complexation: Ambient temperature dehydrogenation of aldehydes and ketones to α,β-unsaturated carbonyl compounds
Nicolaou,Montagnon, Tamsyn,Baran, Phil S.
, p. 993 - 996 (2002)
The reactivity profile of IBX can be altered by complexation with various ligands (e. g. 1-4). A new complex, IBX·MPO, is a remarkably effective oxidant and allows the room-temperature dehydrogenation of carbonyl compounds, for example, the formation of cyclooctenones 6 and 7 from cyclooctanone 5. IBX = iodoxybenzoic acid; MPO = 4-methoxypyridine-N-oxide.
Expedient synthesis of bicyclo[3.2.1]octanes and bicyclo[3.3.1]nonanes via the double Michael addition to cyclic dienones
Moulia, Aurelie,Teo, Joycelyn,Johannes, Charles W.,Richard, Jean-Alexandre
, p. 22882 - 22886 (2013)
We report the expedient synthesis of 8-disubstituted bicyclo[3.2.1]octane- 3-ones and 9-disubstituted bicyclo[3.3.1]octane-3-ones through the double Michael addition (DMA) of carbon nucleophiles to 7 and 8-membered ring dienones. The reaction proceeds in 42-96% yield with an interesting control of the stereochemistry of the bridged secondary, tertiary or quaternary centre.
Asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol
Ferrer, Catalina,Fodran, Peter,Barroso, Santiago,Gibson, Robert,Hopmans, Ellen C.,Damste, Jaap Sinninghe,Schouten, Stefan,Minnaard, Adriaan J.
, p. 2482 - 2492 (2013/06/05)
An efficient asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol is presented employing catalytic asymmetric conjugate addition and catalytic epoxide ring opening as the key steps. Their occurrence in deep sea hydrothermal vents has been
Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones
Diao, Tianning,Stahl, Shannon S.
supporting information; experimental part, p. 14566 - 14569 (2011/10/17)
α,β-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. Here, we report the discovery and application of Pd(DMSO)2(TFA)2 as a catalyst for direct dehydrogenation of cyclohexanones and other cyclic ketones to the corresponding enones, using O2 as the oxidant. The substrate scope includes heterocyclic ketones and several natural-product precursors.