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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 321-331

http://dx.doi.org/10.1351/pac200678020321

3-Aminopyrrolidine lithium amides as chiral ligands for alkyllithium derivatives: Synthesis, NMR analysis, and computational study of their mixed aggregates

Anne Harrison-Marchand1, Jean-Yves Valnot1, Aline Corruble1, Nicolas Duguet1, Hassan Oulyadi2, Stéphanie Desjardins2, Catherine Fressigné1,3 and Jacques Maddaluno1

1 Laboratoire des Fonctions Azotées et Oxygénées Complexes, IRCOF,UMR 6014 CNRS, Université de Rouen, 76821 Mont Saint-Aignan Cédex, France
2 Laboratoire de Chimie Organique et Biologique Structurale, IRCOF,UMR 6014 CNRS, Université de Rouen, 76821 Mont Saint-Aignan Cédex, France
3 Laboratoire de Chimie Théorique, UMR 7616 CNRS, Université Pierre and Marie Curie, 4 place Jussieu, 75252 Paris Cédex 05, France

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  • Lecachey Baptiste, Fressigné Catherine, Oulyadi Hassan, Harrison-Marchand Anne, Maddaluno Jacques: First substoichiometric version of the catalytic enantioselective addition of an alkyllithium to an aldehyde. Chemical Communication 2011, 47, 9915. <http://dx.doi.org/10.1039/c1cc13513a>
  • Pouliquen Mickael, Blanchet Jérôme, Paolis Michaël De, Rema Devi B., Rouden Jacques, Lasne Marie-Claire, Maddaluno Jacques: Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry. Tet Asymm 2010, 21, 1511. <http://dx.doi.org/10.1016/j.tetasy.2010.04.038>
  • Paté Franck, Gérard Hélène, Oulyadi Hassan, de la Lande Aurélien, Harrison-Marchand Anne, Parisel Olivier, Maddaluno Jacques: Shuffling lithiated mixed aggregates: NMR and Car–Parrinello molecular dynamics reveal an unexpected associative pathway. Chem Commun 2009, 319. <http://dx.doi.org/10.1039/b814961e>
  • Davies Stephen G., Garner A. Christopher, Goddard Euan C., Kruchinin Dennis, Roberts Paul M., Smith Andrew D., Rodriguez-Solla Humberto, Thomson James E., Toms Steven M.: Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition. Org Biomol Chem 2007, 5, 1961. <http://dx.doi.org/10.1039/b704932c>
  • Harrison-Marchand Anne, Valnot Jean-Yves, Corruble Aline, Duguet Nicolas, Oulyadi Hassan, Desjardins Stephanie, Fressigne Catherine, Maddaluno Jacques: 3-Aminopyrrolidine Lithium Amides as Chiral Ligands for Alkyllithium Derivatives: Synthesis, NMR Analysis, and Computational Study of Their Mixed Aggregates. ChemInform 2006, 37. <http://dx.doi.org/10.1002/chin.200633274>