Vinyl-aziridines and cyclopropanes in Pd-catalyzed (3+2)-cycloaddition reactions with cyclic N-sulfonyl imines
Efficient palladium-catalyzed (3 + 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....
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| Published in | Tetrahedron Vol. 74; no. 45; pp. 6497 - 6511 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
08.11.2018
Elsevier |
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| Abstract | Efficient palladium-catalyzed (3 + 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 π-allyl palladium intermediates with cyclic N-sulfonyl imines through i) the formation of two NC bonds in the presence of vinylaziridines (synthesis of imidazolidines) and ii) one CC bond and one NC 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 + 2)-cycloaddition reactions. Mechanistic and (intriguing) selectivity outcomes are also going to be discussed.
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| AbstractList | Efficient palladium-catalyzed (3 + 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 π-allyl palladium intermediates with cyclic N-sulfonyl imines through i) the formation of two NC bonds in the presence of vinylaziridines (synthesis of imidazolidines) and ii) one CC bond and one NC 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 + 2)-cycloaddition reactions. Mechanistic and (intriguing) selectivity outcomes are also going to be discussed.
[Display omitted] Efficient palladium-catalyzed (3 + 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 π-allyl palladium intermediates with cyclic N-sulfonyl imines through i) the formation of two NC bonds in the presence of vinylaziridines (synthesis of imidazolidines) and ii) one CC bond and one NC 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 + 2)-cycloaddition reactions. Mechanistic and (intriguing) selectivity outcomes are also going to be discussed. Efficient palladium-catalyzed (3 + 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 pi-allyl palladium intermediates with cyclic N-sulfonyl imines through i) the formation of two N-C bonds in the presence of vinylaziridines (synthesis of imidazolidines) and ii) one C-C bond and one N-C 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 + 2)-cycloaddition reactions. Mechanistic and (intriguing) selectivity outcomes are also going to be discussed. (C) 2018 Elsevier Ltd. All rights reserved. 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. |
| Author | van der Lee, Arie Lebrun, Aurélien Spielmann, Kim Niel, Gilles de Figueiredo, Renata Marcia Campagne, Jean-Marc Tosi, Eleonora |
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| Keywords | Tetrasubstituted carbon Cyclic N-sulfonyl imines Vinyl-aziridines and cyclopropanes (3+2)-cycloaddition reactions Palladium-catalysis ENANTIOSELECTIVE SYNTHESIS NITROGEN-HETEROCYCLES ALPHA,BETA-UNSATURATED ALDEHYDES STEREOSPECIFIC SYNTHESIS DEAROMATIVE 3+2 CYCLOADDITION RING-OPENING CYCLIZATION DIASTEREOSELECTIVE SYNTHESIS SYNERGISTIC CATALYSIS PARA-QUINONE METHIDES KINETIC ASYMMETRIC TRANSFORMATIONS |
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| References | For the use of related reactions using vinyloxazolidinones precursors, see For alternative transition-metal catalyzed reactions involving 2-substituted vinylcyclopropanes, see For a Tentative Explanation on the Observed Enantioselectivities under ‘equilibrating’ Conditions See the Supporting Information. For a non-exhaustive list of (m+n) cycloaddition reactions, see For selected reviews on DYKAT, see (CCDC 1851714), was Deposited with the Cambridge Crystallographic Data Center. For additional information, see the Supporting Information. Wang, Xie, Wang, Zhou (bib28) 2005; 61 Selected examples on Pd-catalyzed ring-opening of vinylaziridines Spielmann, van der Lee, de Figueiredo, Campagne (bib14) 2018; 20 Butler, Inman, Alper (bib1) 2000; 65 (CCDC 1851713), was Deposited with the Cambridge Crystallographic Data Center. For additional information, see the Supporting Information. 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| Snippet | Efficient palladium-catalyzed (3 + 2)-cycloaddition reactions of cyclic N-sulfonyl imines and vinyl-aziridines (or cyclopropanes) have been achieved. The... Efficient palladium-catalyzed (3 + 2)-cycloaddition reactions of cyclic N-sulfonyl imines and vinyl-aziridines (or cyclopropanes) have been achieved. The... Efficient palladium-catalyzed (3 þ 2)-cycloaddition reactions of cyclic N-sulfonyl imines and vinyl-aziridines (or cyclopropanes) have been achieved. The... |
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| SubjectTerms | (3+2)-cycloaddition reactions catalytic activity Chemical Sciences chemical structure Chemistry Chemistry, Organic Cyclic N-sulfonyl imines cycloaddition reactions derivatization diastereoselective synthesis enantioselectivity ethyleneimine imines Organic chemistry palladium Palladium-catalysis Physical Sciences pyrrolidines Science & Technology Tetrasubstituted carbon Vinyl-aziridines and cyclopropanes zwitterions |
| Title | Vinyl-aziridines and cyclopropanes in Pd-catalyzed (3+2)-cycloaddition reactions with cyclic N-sulfonyl imines |
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