77499-85-5Relevant academic research and scientific papers
Diastereoselective synthesis of 3-acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones and their transformation into 3,4-oxolane-fused bicyclic β-lactams
Piens, Nicola,De Craene, Sven,Franceus, Jorick,Mollet, Karen,Van Hecke, Kristof,Desmet, Tom,D'Hooghe, Matthias
, p. 11279 - 11288 (2016/12/07)
cis-3-Acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones were prepared through a Staudinger [2+2]-cyclocondensation between acetoxyketene and the appropriate epoxyimines in a highly diastereoselective way. Subsequent potassium carbonate-mediated acetate hydrolysis, followed by intramolecular ring closure through epoxide ring opening, afforded stereodefined 3-aryl-4-hydroxy-2-oxa-6-azabicyclo[3.2.0]heptan-7-ones as a novel class of C-fused bicyclic β-lactams. Selective benzylic oxidation of bicyclic N-(4-methoxybenzyl)-β-lactams with potassium persulfate and potassium dihydrogen phosphate provided the corresponding N-aroyl derivatives as interesting leads for further β-lactamase inhibitor development.
Diastereoselective synthesis of γ- And δ-lactams from imines and sulfone-substituted anhydrides
Sorto, Nohemy A.,Di Maso, Michael J.,Munoz, Manuel A.,Dougherty, Ryan J.,Fettinger, James C.,Shaw, Jared T.
, p. 2601 - 2610 (2014/04/17)
Sulfone-substituted γ- and δ-lactams have been prepared in a single step with high diastereoselectivity. Sulfonylglutaric anhydrides produce intermediates that readily decarboxylate to provide δ-lactams with high diastereoselectivity. Substituents at the 3- or 4-position of the glutaric anhydride induce high levels of stereocontrol. Sulfonylsuccinic anhydrides produce intermediate carboxylic acids that can be trapped as methyl esters or allowed to decarboxylate under mild conditions. This method has been applied to a short synthesis of the pyrrolizidine alkaloid (±)-isoretronecanol.
RHODIUM(I)-MONO- UND -DIAZADIENEKOMPLEXE, SYNTHESE, SPEKTROSKOPISCHE CHARAKTERISIERUNG, OXIDATIVE ADDITIONSREAKTIONEN UND EINSATZ IN DER HOMOGENEN KATALYSE ZUR HYDROSILYLIERUNG
Brockmann, Monika,Dieck, Heindirk tom,Klaus, Juergen
, p. 209 - 226 (2007/10/02)
The reaction of(Rh(CO)2Cl)2 with di- and monoazadienes gives planar, four-coordinated rhodium(I) complexes Rh(CO)Cl(DAD) (III) and Rh(CO)Cl(MAD)2 (V), respectively, which catalyse the hydrosilylation of alkenes and alkynes.In a stereoselektive cis-addition symmetric internal alkynes give the corresponding silyl alkenes, while the catalytic addition of silane to terminal alkynes leads to the 2-silyl and cis-and trans-1-silyl-alkenes; their ratio depends on the controlling ligand and on the reaction conditions.With a stoichiometric amount of the silane the complexes III react under oxidative addition to give the rhodium(III) complexes Rh(H)(SiR3)(DAD)Cl (VI), which also catalyse the hydrosilylation.
CO-OLIGOMERISATION DE BUTADIENE ET D'HETERODIENES AZOTES CATALYSEE PAR LE NICKEL CONTROLE DE LA SELECTIVITE
Brun, P.,Tenaglia, A,Waegell, B
, p. 5019 - 5030 (2007/10/02)
Nickel (0) catalysed co-oligomerization of butadiene with heterodienes and hetero-olefins is described.It is shown how the selectivity of these reactions can be controlled by the position of the heteroatom in the heteropartner and also by the nature of th
