6395-86-4Relevant academic research and scientific papers
A Catalytic Cross-Olefination of Diazo Compounds with Sulfoxonium Ylides
Neuhaus, James D.,Bauer, Adriano,Pinto, Alexandre,Maulide, Nuno
, p. 16215 - 16218 (2018/11/23)
A ruthenium-catalysed cross-olefination of diazo compounds and sulfoxonium ylides is presented. Our reaction design exploits the intrinsic difference in reactivity of diazo compounds and sulfoxonium ylides as both carbene precursors and nucleophiles, which results in a highly selective reaction.
Catalytic Generation of Donor-Acceptor Cyclopropanes under N-Heterocyclic Carbene Activation and their Stereoselective Reaction with Alkylideneoxindoles
Prieto, Liher,Sánchez-Díez, Eduardo,Uria, Uxue,Reyes, Efraím,Carrillo, Luisa,Vicario, Jose L.
, p. 1678 - 1683 (2017/05/22)
Formylcyclopropanes undergo activation in the presence of an N-heterocyclic carbene catalyst generating a donor-acceptor cyclopropane intermediate with the ability to undergo ring-opening followed by formal [4+2] cycloaddition with alkylideneoxindoles. This enables the direct enantio- and diastereoselective synthesis of tetrahydropyrano[2,3-b]indoles through the use of a chiral NHC catalyst. (Figure presented.).
Organocatalysed synthesis of isoxazolines initiated by a chemoselective oxa-Michael reaction of N-BocNHOH
Noel,Gembus,Levacher,Briere
supporting information, p. 1245 - 1249 (2014/03/21)
An organocatalysed and chemoselective one-pot oxa-Michael-cyclocondensation reaction of N-BocNHOH to unsaturated α-ketoesters is reported which affords an original entry to enantioenriched 3-isoxazoline carboxylate derivatives as biorelevant heterocyclic
Metal-free michael-addition-initiated three-component reaction for the regioselective synthesis of highly functionalized pyridines: Scope, mechanistic investigations and applications
Allais, Christophe,Lieby-Muller, Frederic,Rodriguez, Jean,Constantieux, Thierry
supporting information, p. 4131 - 4145 (2013/07/19)
A metal-free and completely regioselective three-component synthesis of highly functionalized pyridines from 1,3-dicarbonyl derivatives and Michael acceptors has been achieved. Activated Michael acceptors, that is, β,γ-unsaturated α-oxo carbonyl derivatives, were utilized, allowing substitution at the 4-position and remarkable functional diversity at the 2-position of the pyridine ring. The scope and limitations of this environmentally friendly domino reaction are disclosed, with full experimental data, and the results of mechanistic investigations are discussed. The three-component synthesis of polysubstituted pyridines starting from 1,3-dicarbonyl compounds, α,β-unsaturated carbonyl derivatives and ammonium acetate has been studied, including the scope and mechanism. This methodology is a rare example of a totally regioselective multicomponent access to highly substituted pyridines that complies with many of the stringent criteria of sustainable chemistry. Copyright
Enantioselective copper-catalyzed conjugate addition of trimethylaluminium to β,γ-unsaturated α-ketoesters
Gremaud, Ludovic,Alexakis, Alexandre
, p. 794 - 797 (2012/03/09)
Not a cop out: The copper-catalyzed asymmetric conjugate addition of organometallic reagents to Michael acceptors is an important methodology for forming a C-C bond in an enantioselective manner. Such an addition of Me 3Al to β,γ-unsaturated α-
On the Use of 3-Bromopropyne as a Reagent for the Introduction of the Pyruvate Moiety
Chen, Chen,Crich, David
, p. 1289 - 1290 (2007/10/02)
In the presence of metallic zinc 3-bromopropyne reacts with aldehydes to give homopropynylic alcohols which are converted to the corresponding bromohomopropynylic acetates by acetylation followed by reaction with N-bromosuccinimide and a catalytic quantity of silver acetate; these derivatives are then oxidized to γ-acetoxy-α-ketoesters with osmium tetroxide and tert-butyl hydroperoxide resulting in a convenient four step sequence for the introduction of the pyruvate moiety.
