Vinyl-aziridines and cyclopropanes in Pd-catalyzed (3+2)-cycloaddition reactions with cyclic N-sulfonyl imines
| Autor: | Gilles Niel, Arie van der Lee, Eleonora Tosi, Renata Marcia de Figueiredo, Aurélien Lebrun, Kim Spielmann, Jean-Marc Campagne |
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| Přispěvatelé: | Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Institut Européen des membranes (IEM), Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM) |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
010402 general chemistry
01 natural sciences Biochemistry Medicinal chemistry Pyrrolidine Cyclopropane chemistry.chemical_compound Imidazolidine Drug Discovery Imidazolidines (3+2)-cycloaddition reactions Sulfonyl chemistry.chemical_classification 010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Enantioselective synthesis Vinyl-aziridines and cyclopropanes Aziridine Cycloaddition 3. Good health 0104 chemical sciences chemistry Cyclic N-sulfonyl imines Palladium-catalysis Tetrasubstituted carbon |
| Zdroj: | Tetrahedron Tetrahedron, Elsevier, 2018, 74 (45), pp.6497-6511. ⟨10.1016/j.tet.2018.09.040⟩ |
| ISSN: | 0040-4020 |
| Popis: | International audience; Efficient palladium-catalyzed (3 þ 2)-cycloaddition reactions of cyclic N-sulfonyl imines and vinyl-aziridines (or cyclopropanes) have been achieved. The reactions, with either vinylic substrate, proceed with excellent yields affording highly functionalized imidazolidine and pyrrolidine derivatives. The cycloadditions take place via the reaction of zwitterionic p -allyl palladium intermediates with cyclic N-sulfonyl imines through i) the formation of two NeC bonds in the presence of vinylaziridines (synthesis of imidazolidines) and ii) one CeC bond and one NeC bond in the presence of vinylcyclopropanes (synthesis of pyrrolidines). Following on preliminary works on the diastereoselective synthesis of imidazolidines, herein we wish to give a broader view on the subject by describing derivatization reactions and attempts towards an enantioselective version. Moreover, we describe and discuss the behavior of each vinylic substrate (aziridine or cyclopropane) on the (3 þ 2)-cycloaddition reactions. Mechanistic and (intriguing) selectivity outcomes are also going to be discussed. |
| Databáze: | OpenAIRE |
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