90020-41-0Relevant academic research and scientific papers
Stereocontrolled preparation of bicyclic alkaloid analogues: an approach towards the kinabalurine skeleton
Kavanagh, Yvonne,O'Brien, Matthew,Evans, Paul
experimental part, p. 8259 - 8268 (2009/12/24)
An approach towards the construction of bicyclic analogues of monoterpene alkaloids belonging to the kinabalurine, incarvilline and skytanthine families of natural products is reported. These syntheses rely on a stereoselective intramolecular Pauson-Khand
Remarkably Facile Hexatriene Electrocyclizations as a Route to Functionalized Cyclohexenones via Ring Expansion of Cyclobutenones
Magomedov, Nabi A.,Ruggiero, Piero L.,Tang, Yuchen
, p. 1624 - 1625 (2007/10/03)
This Communication describes a cascade reaction sequence that leads to highly functionalized cyclohexenones starting from reaction of cyclobutenones with α-lithio-α,β-unsaturated sulfones and amides. The hexatriene-cyclohexadiene cyclization steps presumed to be involved in these transformations are among the most facile hexatriene electrocyclizations reported thus far. Copyright
Palladium-catalyzed cascade reaction of α,β-unsaturated sulfones with aryl iodides
Mauleon, Pablo,Nunez, Angel A.,Alonso, Ines,Carretero, Juan C.
, p. 1511 - 1520 (2007/10/03)
Unlike traditionally used acyclic 1,2-disubstituted alkenes, the reaction of α,β-unsaturated phenyl sulfones with aryl iodides under Heck reaction conditions (Pd(OAc)2 as catalyst, Ag2-CO3 as base in DMF at 120°C) takes place mainly by a cascade process, involving one unit of the alkene and three units of the aryl iodide, to afford a substituted 9-phenylsulfonyl-9,10-dihydrophenanthrene, The dominant formation of this 3:1 coupling product, instead of the Heck trisubstituted olefin, shows that aromatic C-H activation processes can compete with the usually fast syn β-hydrogen elimination step in the Heck arylation of an acyclic olefin. The structural scope of this palladium-catalyzed cascade arylation of α,β-unsaturated sulfones has proved to be wide with regard to substitution at the β-position (alkyl, aryl, or alkenyl substitution), substitution at the sulfone unit (alkyl or phenyl sulfones), and configuration at the C=C bond (trans or cis). Moreover, although less favored than in the case of the arylation of α,β-unsaturated sulfones, similarly substituted 9,10-dihydrophenanthrenes have also been obtained in the case of α,β-unsaturated phosphine oxides and α,β-unsaturated phosphonate esters. A Pd0-pdII-pdIV mechanistic pathway involving the successive formation of highly electrophilic σ-alkylpalladium intermediates and palladacycles is proposed for this multi-component arylation.
Samarium(II) iodide-mediated deoxygenative debromination of α-bromo-β-hydroxy (acetoxy) phenyl sulfones: Synthesis of α,β-unsaturated sulfones
Reutrakul, Vichai,Jarussophon, Suwatchai,Pohmakotr, Manat,Chaiyasut, Yupa,U-Thet, Saengvimon,Tuchinda, Patoomratana
, p. 2285 - 2288 (2007/10/03)
Deoxygenative debromination of α-bromo-β-hydroxy (acetoxy) phenyl sulfones with samarium(II) iodide led to substituted α,β-unsaturated sulfones in good to excellent yields. The E-isomer is the major product. A possible mechanism via an α-sulfonyl radical pathway is proposed.
IODINE ATOM TRANSFER ADDITION REACTIONS WITH ALKYNES. PART 1: ALKYL IODIDES
Curran, Dennis P.,Kim, Dooseop
, p. 6171 - 6188 (2007/10/02)
Simple 2*- and 3*- alkyl iodides add smoothly to electron deficient alkynes under standard atom transfer conditions (10percent Bu3SnSnBu3), sunlamp photolysis).Mechanistic experiments help to interpret stereochemical and yield trends, and a new model for
α-bENZENESULFONYL FREE RADICALS
Julia, M.,Rolando, C.,Verpeaux, J.N.
, p. 4319 - 4320 (2007/10/02)
Allylic α-halosulfones give, on reduction with tri n-butyl tin hydride, sizeable amounts of dimers.It so appears that free radicals can indeed be formed α to an arenesulfonyl group and coupling can occur during tin hydride reduction of halides
Synthesis of α,β-γ,δ-unsaturated sulfones and sulfoxides via the Horner-Emmons reaction
Jong, B. E. de,Koning, H. de,Huisman, H. O.
, p. 410 - 414 (2007/10/02)
α,β-γ,δ-Unsaturated sulfones and sulfoxides have been prepared via the Horner-Emmons reaction of α,β-unsaturated carbonyl compounds with α-phosphoryl sulfones and sulfoxides.
