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Synthèse de cyclopropanes substitués par des couplages catalysés au palladium

Abstract : Cyclopropanes are encountered in several natural and synthetic products displaying a wide range of biological activities. The goal of our studies has been the development of palladium-catalyzed cross coupling reactions allowing access to diversely substituted and functionalized cyclopropanes. Suzuki-Miyaura cross-couplings involving potassium cis- and trans-2-benzyloxy-cyclopropyltrifluoroborates have been successfully developed after an important optimization work. The synthesis of aminocyclopropanes by Hartwig-Buchwald cross-couplings involving cyclopropyl iodides turned out to be more difficult to achieve. The feasibility of such couplings was demonstrated with an example, dealing with an intramolecular reaction, but the results could not be generalized. The first examples of Sonogashira cross-couplings of diversely substituted cyclopropyl iodides with terminal alkynes have been described. The corresponding alkynylcyclopropanes were obtained with excellent yields and with retention of configuration. The cis-2-alkynylcyclopropanecarboxamides prepared by this strategy can be subsequently involved in a 5 exo dig cyclization under basic conditions to provide enamides incorporating a 3 azabicyclo[3.1.0]hexane moiety. Under acid conditions, these compounds generate bicyclic N-acyliminium ions that can be involved in ionic reductions or Pictet-Spengler cyclizations to provide a wide variety of structurally complex heterocyclic compounds with complete diastereoselectivity
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Submitted on : Thursday, May 30, 2013 - 5:03:33 PM
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  • HAL Id : tel-00828335, version 1


Benoît de Carné-Carnavalet. Synthèse de cyclopropanes substitués par des couplages catalysés au palladium. Chimie organique. Université Pierre et Marie Curie - Paris VI, 2012. Français. ⟨NNT : 2012PAO66650⟩. ⟨tel-00828335⟩



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