Palladium‐Mediated [2+1] Cycloaddition of Norbornene Derivatives with Ynamides
作者： Gérard Buono , Hervé Clavier , Aymeric Lepronier , Nathalie Bengobesse-Mintsa , David Gatineau
关键词:
摘要: An efficient palladium-catalyzed [2 + 1]cycloaddition between ynamides and norbornenes or norbornadienes is reported. Both phosphapalla- dacycles palladium/secondary phosphine oxide catalytic systems were found to be competent for the transformation allowing preparation of ami- nomethylenecyclopropanes. The reaction showed general applicability various functionalized bicyclo[2.2.1]hept-2-enes ynamides. A chiral phosphapalladacycle was tested carry out this in an enantioselective fashion.
archives-ouvertes.fr
sci-hub.se 参考文章(58)
Jiri Zemlicka, Methylenecyclopropane Analogues of Nucleosides as Anti-herpes Agents Advances in Antiviral Drug Design. ,vol. 5, pp. 113- 165 ,(2007) , 10.1016/S1075-8593(06)05003-9
Hervé Clavier, Karel Le Jeune, Innocenzo de Riggi, Alphonse Tenaglia, Gérard Buono, Highly Selective Cobalt-Mediated [6 + 2] Cycloaddition of Cycloheptatriene and Allenes Organic Letters. ,vol. 13, pp. 308- 311 ,(2011) , 10.1021/OL102783X
Fernando López, Alejandro Delgado, J. Ramón Rodríguez, Luis Castedo, José L. Mascareñas, Ruthenium-Catalyzed [3 + 2] Intramolecular Cycloaddition of Alk-5-ynylidenecyclopropanes Promoted by the “First-Generation” Grubbs Carbene Complex Journal of the American Chemical Society. ,vol. 126, pp. 10262- 10263 ,(2004) , 10.1021/JA0480466
Moisés Gulías, Juan Durán, Fernando López, Luis Castedo, Jose L. Mascareñas, Palladium-catalyzed [4+3] intramolecular cycloaddition of alkylidenecyclopropanes and dienes. Journal of the American Chemical Society. ,vol. 129, pp. 11026- 11027 ,(2007) , 10.1021/JA0756467
Lutz Ackermann, Robert Born, Julia H. Spatz, Andreas Althammer, Christian J. Gschrei, Air-stable phosphine oxides as preligands for catalytic activation reactions of C-Cl, C-F, and C-H bonds Pure and Applied Chemistry. ,vol. 78, pp. 209- 214 ,(2006) , 10.1351/PAC200678020209
Crina Cismaş, Nicolas Vanthuyne, Hélène Rispaud, Richard Attila Varga, Elena Bogdan, Christian Roussel, Ion Grosu, Geometric enantiomerism in cyclic compounds: chiral dibrominated 1,3-dioxanes. Chirality. ,vol. 23, pp. 167- 171 ,(2011) , 10.1002/CHIR.20895
Ahmad Masarwa, Ilan Marek, Selectivity in Metal-Catalyzed Carbon ? Carbon Bond Cleavage of Alkylidenecyclopropanes Chemistry: A European Journal. ,vol. 16, pp. 9712- 9721 ,(2010) , 10.1002/CHEM.201001246
Jürg Krebs, Dominik Guggisberg, Urs Stämpfli, Markus Neuenschwander, Synthese von Triafulven-Vorstufen für Retro-Diels-Alder-Reaktionen† Helvetica Chimica Acta. ,vol. 69, pp. 835- 848 ,(1986) , 10.1002/HLCA.19860690410
Aileen T. McNichols, Peter J. Stang, Diana M. Addington, Brian Halton, The preparation of exocyclic functionalised alkylidenecycloproparanes via a new procedure Tetrahedron Letters. ,vol. 35, pp. 437- 440 ,(1994) , 10.1016/0040-4039(94)85074-7
Changmei Cheng, Tetsuro Shimo, Kenichi Somekawa, Masanori Baba, 9-Hydroxymethylcyclopropylidenemethylenyladenine: The design, facile synthesis, isomer separation and anti-HIV-1 activities Tetrahedron. ,vol. 54, pp. 2031- 2040 ,(1998) , 10.1016/S0040-4020(97)10413-6