88726-07-2Relevant articles and documents
Fine tuning of the [2+2] vs [4+2] selectivity of 1,1-disubstituted dienes in cycloaddition reactions
Zoller,Breuilles,Klein,Uguen,De Cian,Fischer
, p. 9015 - 9018 (1999)
β-Arylsulfonyl vinylketones have been shown to react, both inter and intramolecularly, with 1,1-disubstituted dienes to afford, depending on the used -i.e. thermal or Lewis-acid catalysed-conditions, either [4+2] or [2+2] cycloadducts, respectively.
Regioselective and stereoselective sulfonylation of alkynylcarbonyl compounds in water
Li, Wenyi,Yin, Guoxing,Huang, Lei,Xiao, Yan,Fu, Zhimin,Xin, Xiu,Liu, Fang,Li, Zhizhang,He, Weimin
, p. 4879 - 4883 (2016/10/06)
With water as the reaction medium, an efficient protocol has been developed for the synthesis of Z-β-sulfonyl-α,β-unsaturated carbonyl products via water-promoted sulfonylation of alkynylcarbonyl compounds with sodium sulfinates. This strategy could effectively avoid the use of toxic organic solvents, catalysts and additives. This method features a wide substrate scope with a broad range of functional group tolerance, utilizes easily available starting materials, can be scaled-up, and is operationally simple.
High 1,2-Asymmetric Induction in Radical Reactions: Radical Addition to γ-Hydroxy α,β-Unsaturated Carboxylic Esters and Sulfones
Ogura, Katsuyuki,Kayano, Akio,Akazome, Motohiro
, p. 3091 - 3101 (2007/10/03)
High 1,2-asymmetric induction was realized by the addition of a 1-hydroxy-1 -methylethyl radical to conformationally flexible (E)-γ-hydroxy α,β-unsaturated carboxylic esters and sulfones (1 and 2, respectively). Upon the irradiation (> 290 nm) of (E)-1 and benzophenone in 2-propanol, the 1-hydroxy-1-methylethyl radical was generated in situ and added to (E)-1 with high anti-stereoselectivity. The bulkier is the γ-alkyl group of (E)-1, the higher does the selectivity become. Similarly, a radical addition to the acetates of (E)-1 and (E)-2 proceeded stereoselectively in an anti fashion, whereas (Z)-2 exhibited syn-stereoselectivity. The mechanism for these stereoselective radical additions is discussed.
INDUCTION PAR LA LUMIERE DE L'OXYDATION DES COMPLEXES Η3-ALLYLPALLADIUM PAR L'OXYGENE MOLECULAIRE
Muzart, J.,Pale, P.,Pete, J.P.,Riahi, A.
, p. 731 - 739 (2007/10/02)
Irradiation at λ=366 nm of oxygenated solutions of η3-allylpalladium complexes leads to unsaturated carbonyl compounds.Substitution of the η3-allyl ligand by an electron withdrawing group could induce a regioselective oxidation of the allylic position farthest from this group.The efficiency of these reactions is sensible to the nature of the solvent.
Regio- and Stereo-selective Synthesis of β-Sulphonyl-α,β-Unsaturated Carbonyl Compounds via an Iodosulphonylation-Dehydroiodination Raction
Najera, Carmen,Baldo, Beatriz,Yus, Miguel
, p. 1029 - 1032 (2007/10/02)
α,β-Unsaturated carbonyl compounds underwent regiospecific iodosulphonylation with toluene-p-sulphonyl iodide or sodium toluene-p-sulphinate and iodine to afford products (2), which were stereoselectively dehydroiodinated by triethylamine to give β-sulphonyl derivatives (3).The reactivity of compounds (3) as cationic β-acylvinyl equivalents, tested with amines or thiophenol, gave compounds (4) resulting from a displacement reaction.
