174875-59-3Relevant academic research and scientific papers
N-acyliminium ion chemistry: Highly efficient and versatile carbon-carbon bond formation by nucleophilic substitution of hydroxy groups catalyzed by Sn(NTf2)4
Othman, Raja Ben,Affani, Radouane,Tranchant, Marie-Jose,Antoniotti, Sylvain,Dalla, Vincent,Dunach, Elisabet
supporting information; experimental part, p. 776 - 780 (2010/04/24)
(Chemical Equation Presentation) Atom-economical: Unmodified hemiN,O-acetals are used in a catalytic, highly efficient α- amidoalkylation of a broad range of carbon-centered nucleophiles, including silicon-based components, active methylene derivatives, electron-rich arenes, and even simple ketones (see scheme). The reactions proceed in a highly efficient manner and typically require only 1 mol% of the Lewis super-acidic reagent Sn(NTf2)4 as the catalyst.
Synthesis of BINOL derived phosphorodithioic acids as new chiral Br?nsted acids and an improved synthesis of 3,3′-disubstituted H8-BINOL derivatives
Pousse, Guillaume,Devineau, Alice,Dalla, Vincent,Humphreys, Luke,Lasne, Marie-Claire,Rouden, Jacques,Blanchet, Jér?me
scheme or table, p. 10617 - 10622 (2010/01/16)
Original phosphorodithioic acid diesters were prepared according to an improved synthesis of 3,3′-disubstituted H8-BINOL derivatives. In preliminary experiments, these new Br?nsted acids were tested as organocatalysts in three reactions. They promoted the Nazarov cyclisation with mixed selectivities, the Mannich reaction with good enantioselectivity and they catalyzed efficiently the alkylation of N-acyliminium with enol silyl ether.
Eco-friendly N-acyliminium ion chemistry: solvent-free HNTf2 and TIPSOTf-catalyzed α-amidoalkylation of silicon-based π-nucleophiles
Tranchant, Marie-José,Moine, Charlotte,Othman, Raja Ben,Bousquet, Till,Othman, Mohamed,Dalla, Vincent
, p. 4477 - 4480 (2007/10/03)
The α-amidoalkylation of silicon-based π-nucleophiles is efficiently catalyzed by HNTf2 or TIPSOTf at very low levels of loading in neat conditions.
Synthesis of bicyclic guanidines from pyrrolidin-2-one
Louwrier, Saskia,Tuynman, Antonin,Hiemstra, Henk
, p. 2629 - 2646 (2007/10/03)
The syntheses of three bicyclic guanidines as model compounds for the guanidine alkaloid ptilomycalin A are described. The guanidines are prepared from pyrrolidin-2-one via an N-acyliminium ion coupling reaction with silyl enol ethers and a direct guanylation with bis-Boc-thiourea and HgCl2 as the key steps.
