Diastereoselective Palladium-Catalyzed (3 + 2)-Cycloadditions from Cyclic Imines and Vinyl Aziridines
| Autor: | Renata Marcia de Figueiredo, Jean-Marc Campagne, Arie van der Lee, Kim Spielmann |
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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 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) |
| Rok vydání: | 2018 |
| Předmět: |
[CHIM.ORGA]Chemical Sciences/Organic chemistry
010405 organic chemistry Chemistry Organic Chemistry chemistry.chemical_element 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Imidazolidine Yield (chemistry) Aminal Physical and Theoretical Chemistry Imidazolidines ComputingMilieux_MISCELLANEOUS Palladium |
| Zdroj: | Organic Letters Organic Letters, American Chemical Society, 2018, 20 (5), pp.1444-1447. ⟨10.1021/acs.orglett.8b00228⟩ |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.8b00228 |
| Popis: | The synthesis of cyclic imidazolidines via two N–C bond-forming sequences has been developed. The transformation goes through a (3 + 2)-cycloaddition reaction in the presence of catalytic amounts of palladium by combining several vinyl aziridines and cyclic N-sulfonyl imines. Interestingly, the use of LiCl as additive allowed the improvement of diastereoselectivities when less encumbered substrates were used. The imidazolidine derivatives that bear aminal cores are isolated in high yields (15 examples, up to 96% yield) and diastereoselectivities (up to >20:1). |
| Databáze: | OpenAIRE |
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