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

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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  • Su Chicheung, Hopson Russell, Williard Paul G.: Influence of Steric Factors on Chiral Lithium Amide Aggregates. J. Am. Chem. Soc. 2014, 136, 3246. <>
  • Harrison-Marchand Anne, Mongin Florence: Mixed AggregAte (MAA): A Single Concept for All Dipolar Organometallic Aggregates. 1. Structural Data. Chem. Rev. 2013, 113, 7470. <>
  • Mongin Florence, Harrison-Marchand Anne: Mixed AggregAte (MAA): A Single Concept for All Dipolar Organometallic Aggregates. 2. Syntheses and Reactivities of Homo/HeteroMAAs. Chem. Rev. 2013, 113, 7563. <>
  • Reich Hans J.: Role of Organolithium Aggregates and Mixed Aggregates in Organolithium Mechanisms. Chem. Rev. 2013, 113, 7130. <>
  • Su Chicheung, Hopson Russell, Williard Paul G.: Mixed Aggregates of an Alkyl Lithium Reagent and a Chiral Lithium Amide Derived from N-Ethyl-O-triisopropylsilyl Valinol. J. Am. Chem. Soc. 2013, 135, 14367. <>
  • Harrison-Marchand Anne, Gérard Hélène, Maddaluno Jacques: Catalytic enantioselective nucleophilic addition of organolithium derivatives: pitfalls and opportunities. New J. Chem. 2012, 36, 2441. <>
  • 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. <>
  • 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. <>
  • Jahn Ullrich, Kafka František, Pohl Radek, Jones Peter G.: N,3,4-Trisubstituted pyrrolidines by electron transfer-induced oxidative cyclizations of N-allylic β-amino ester enolates. Tetrahedron 2009, 65, 10917. <>
  • 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. <>
  • Paté Franck, Oulyadi Hassan, Harrison-Marchand Anne, Maddaluno Jacques: 6Li NMR Study of the Equilibrium between Methyllithium and n-Butyllithium in THF. Influence of a Third Partner, a Chiral Lithium Amide. Organometallics 2008, 27, 3564. <>
  • 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. <>
  • 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. <>