64505-07-3Relevant articles and documents
Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds
Yang, Tonghao,Lin, Yajun,Yang, Chaoqun,Yu, Wei
supporting information, p. 6097 - 6102 (2019/11/20)
Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds provides a simple and atom-economical approach toward enamides and isoquinolones. This paper reports two catalyst systems for these transformations which employ iron(ii) complexes [Fe(dpbz)]Br2 (dpbz = 1,2-bis(diphenylphosphino)benzene) and FeBr2/Et3N, respectively. [Fe(dpbz)]Br2 was found to be highly effective at converting 2-azido-2,3-dihydro-1H-inden-1-ones to isoquinolones. The reagent combination of FeBr2/Et3N, on the other hand, exhibited a broader catalytic scope, owing to the beneficial effect of Et3N. This latter catalyst system enables 2-azido-2-methyl-1,3-dicarbonyl compounds to be converted to the corresponding enamides under mild conditions in good yields.
Asymmetric transfer hydrogenation of α,β-unsaturated, α-tosyloxy and α-substituted ketones
Peach, Philip,Cross, David J.,Kenny, Jennifer A.,Mann, Inderjit,Houson, Ian,Campbell, Lynne,Walsgrove, Tim,Wills, Martin
, p. 1864 - 1876 (2007/10/03)
Asymmetric transfer hydrogenation of cyclic and acyclic α,β-unsaturated ketones catalysed by η6-p-cymene/ ruthenium(II) and η5-pentamethylcyclopentadienyl/rhodium(III) complexes have been investigated. Cyclic α,β-unsaturated ketones appeared to be more suitable substrates for the synthesis of enantiomerically pure allylic alcohols than do acyclic α,β-unsaturated ketones. A proposed mechanism for the formation of 4-phenyl-[1,3]-dioxolan-2-one from α-tosyloxy- and halo-substituted acetophenones is discussed. The results of further investigations into the reduction of a range of α- tosyloxyacetophenones and the dynamic kinetic resolution of α-substituted ketones is presented.
Decomposition of 2-Azido Ketones to 2-(Acetylamino)-2-alken-1-ones by Perrhenate Catalysis
Effenberger, Franz,Beisswenger, Thomas,Az, Rainer
, p. 4869 - 4876 (2007/10/02)
The thermally induced elimination of nitrogen from cyclic and acyclic 2-azido ketones 2 is accelerated by catalytic amounts of perrhenate.In acetic anhydride - if necessary in the presence of small amounts of a mineral acid - 2-(acetylamino)-2-alken-1-ones 3 are formed in good yields.The decomposition rates of the catalysed and the uncatalysed thermolysis are compared.