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UID:69e0eb3575442
DTSTAMP:20260416T095917
DTSTART:20130603T110000
SEQUENCE:0
TRANSP:OPAQUE
DTEND:20130603T123000
URL:https://murmitoyen.com/events/vanille/udem/detail/181281
LOCATION:Université de Montréal - Pavillon Claire-McNicoll\, 2900\, chemi
 n de la Tour\, Montréal\, QC\, Canada\, H3T 1J6
SUMMARY:Conférence du Professeur Jérôme Waser (EPFL)
DESCRIPTION:Titre : Electrophilic Alkynylation of Olefins and Annulation Re
 actions of Aminocyclopropanes.Cette conférence sera prononcée en anglais
  par le professeur Jérôme Waser du laboratoire de catalyse et synthèse 
 organique au sein de l'École polytechnique fédérale de Lausanne (Suisse
 ). Ce dernier sera à Montréal dans le cadre d'une tournée de conférenc
 es en Amérique du Nord.Résumé : The use of organic molecules of increas
 ing complexity is one of the major motors of progress in multiple fields o
 f fundamental and applied science\, such as chemical biology\, drug discov
 ery or organic materials. To answer these needs\, it is crucial to develop
  new reactions for a fast access into molecular complexity. Our group make
 s use of the power of catalysis to develop new reactions basedon the excep
 tional reactivity of electrophilic acetylenes and aminocyclopropanes.Acety
 lenes: The triple bond is one of the most versatile functional groups in o
 rganic chemistry\, material sciences and chemical biology. Most alkyne-tra
 nsfer reactions have been limited to the nucleophilic addition of acetylid
 es to electrophiles. The development of efficient electrophilic alkynylati
 on methods would give access to structurally completely different acetylen
 es. Our group has introduced EthynylBenziodoXolone (EBX) hypervalent iodin
 e reagents for direct alkyne-transfer to C=C bonds. The use of a palladium
 (II) catalyst combined with EBX reagents led to the first intramolecular o
 xy- and amino- alkynylation of olefins for the synthesis of lactones\, lac
 tams\, oxazolidinones and imidazolidinones. On the other hand\, a palladiu
 m(0) catalyst together with alkynyl bromides could be used to access tetra
 hydrofurans and pyrrolidines starting from alcohols and amines.Aminocyclop
 ropanes: Activation of cyclopropanes with an amino and a carbonyl group le
 d to exceptional reactivity\, both in cyclization and annulation reactions
 . Selective cyclization on the carbon or nitrogen of indole heterocycles u
 sing either copper or Brønsted acid catalysts allowed the synthesis of th
 e alkaloids aspidospermidine and goniomitine. Using Phthalimido-substitute
 d cyclopropanes together with iron or tin catalysts\, a highly diastereose
 lective and enantiospecific [3+2] annulation reaction with enol ethers and
  carbonyls gave access to multi-substituted cyclopentyl- and tetrahydrofur
 yl amines\, key structural elements of both DNA and bioactive compounds.In
 formation supplémentaire
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