Intramolecular vinylation of carbanions using N -acyl benzomorpholines as masked vinylureas and vinylcarbamates
| العنوان: | Intramolecular vinylation of carbanions using N -acyl benzomorpholines as masked vinylureas and vinylcarbamates |
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| المؤلفون: | Johnathan V. Matlock, Brian P. Corbet, Josep Mas-Roselló, Jonathan Clayden |
| المساهمون: | Synthetic Organic Chemistry |
| المصدر: | Corbet, B, Matlock, J, Mas Rosello, J & Clayden, J 2017, ' Intramolecular vinylation of carbanions using N-acyl benzomorpholines as masked vinylureas and vinylcarbamates ', Comptes Rendus Chimie, vol. 20, no. 6, pp. 634-642 . https://doi.org/10.1016/j.crci.2017.01.006Test Comptes Rendus Chimie, 20(6), 634-642. ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER |
| بيانات النشر: | Elsevier BV, 2017. |
| سنة النشر: | 2017 |
| مصطلحات موضوعية: | Nitrile, General Chemical Engineering, Substituent, Hydantoin, macromolecular substances, Benzomorpholine, 010402 general chemistry, Benzylic anions, ORGANOLITHIUM COMPOUNDS, 01 natural sciences, Medicinal chemistry, ALPHA-ARYLATION, chemistry.chemical_compound, Vinylation, Organic chemistry, LITHIATED UREAS, Tertiary stereocentre, ASYMMETRIC-SYNTHESIS, Carbanion, 010405 organic chemistry, ARYL MIGRATION, DIARYLMETHYLAMINES, organic chemicals, Aryl, technology, industry, and agriculture, Enantioselective synthesis, AMINES, General Chemistry, Lithium diisopropylamide, Isocyanate, 0104 chemical sciences, CARBOLITHIATION, chemistry, TERTIARY ALCOHOLS, METALATED UREAS |
| الوصف: | Treatment of urea or carbamate derived benzomorpholines with lithium diisopropylamide generates N-vinyl ureas or N-vinyl carbamates by elimination of a phenoxide anion, cleaving the benzomorpholine ring. Simultaneous formation of a carbanion a to a stabilising aryl or nitrile group allows migration of the newly formed N-vinyl substituent to the carbanionic centre, in some cases with high enantiospecificity. Mild hydrolysis of the resulting urea or carbamate returns a C-vinylated amine, alcohol or hydantoin, in some cases with high enantiomeric purity. This 'masked' vinylation strategy avoids the need to use the reactive and volatile vinyl isocyanate as a starting material. (C) 2017 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved. |
| وصف الملف: | application/pdf |
| تدمد: | 1631-0748 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::5ed2653ddf12a77e42a957a307b4df2eTest https://doi.org/10.1016/j.crci.2017.01.006Test |
| حقوق: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....5ed2653ddf12a77e42a957a307b4df2e |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 16310748 |
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