Ritter-enabled catalytic asymmetric chloroamidation of olefins†
| العنوان: | Ritter-enabled catalytic asymmetric chloroamidation of olefins† |
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| المؤلفون: | Aritra Sarkar, Cecilia C Morgenstern, Richard J. Staples, Bardia Soltanzadeh, Babak Borhan, Daniel C Steigerwald |
| المصدر: | Chemical Science |
| بيانات النشر: | The Royal Society of Chemistry, 2020. |
| سنة النشر: | 2020 |
| مصطلحات موضوعية: | chemistry.chemical_classification, General Chemistry, Electrophilic aromatic substitution, Combinatorial chemistry, Sulfonamide, Catalysis, chemistry.chemical_compound, Chemistry, Nucleophile, chemistry, Reagent, Enantiomeric excess, Guanidine, Alkyl |
| الوصف: | Intermolecular asymmetric haloamination reactions are challenging due to the inherently high halenium affinity (HalA) of the nitrogen atom, which often leads to N-halogenated products as a kinetic trap. To circumvent this issue, acetonitrile, possessing a low HalA, was used as the nucleophile in the catalytic asymmetric Ritter-type chloroamidation of allyl-amides. This method is compatible with Z and E alkenes with both alkyl and aromatic substitution. Mild acidic workup reveals the 1,2-chloroamide products with enantiomeric excess greater than 95% for many examples. We also report the successful use of the sulfonamide chlorenium reagent dichloramine-T in this chlorenium-initiated catalytic asymmetric Ritter-type reaction. Facile modifications lead to chiral imidazoline, guanidine, and orthogonally protected 1,2,3 chiral tri-amines. Intermolecular haloamination reactions are challenging due to the high halenium affinity of the nitrogen atom. This is circumvented by using acetonitrile as an attenuated nucleophile, resulting in an enantioselective halo-Ritter reaction. |
| اللغة: | English |
| تدمد: | 2041-6539 2041-6520 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8c5075df2340a4b300a741b0b74f9efb http://europepmc.org/articles/PMC8179065 |
| حقوق: | OPEN |
| رقم الأكسشن: | edsair.doi.dedup.....8c5075df2340a4b300a741b0b74f9efb |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 20416539 20416520 |
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