Zinc-Mediated Double Addition on Functionalized Nitriles
| Autor: | Philippe Bertus, M. S. M. Pearson-Long, Julien Caillé, Fabien Boeda, Mathilde Pantin |
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| Přispěvatelé: | Institut des Molécules et Matériaux du Mans (IMMM), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Nucleophilic addition
010405 organic chemistry Chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry zinc chemistry.chemical_element Zinc 010402 general chemistry 01 natural sciences Combinatorial chemistry Kinetic control Catalysis 0104 chemical sciences organometallic reagents tertiary carbinamines nucleophilic addition Nucleophile Nitrogen atom Reagent Moiety nitriles Chemoselectivity allylation |
| Zdroj: | SYNTHESIS SYNTHESIS, Georg Thieme Verlag, 2019, 51 (06), pp.1329-1341. ⟨10.1055/s-0037-1611704⟩ |
| ISSN: | 0039-7881 1437-210X |
| DOI: | 10.1055/s-0037-1611704⟩ |
| Popis: | International audience; Allylzinc reagents were used to access highly functionalized tertiary carbinamine derivatives in high yields from cyanoesters and cyanocarbonates. While the monoaddition of organometallics on nitriles is generally observed, in this work the nucleophilic allylation occurs twice, due to an intermediate transfer of the carbonyl moiety onto the nitrogen atom. The chemoselectivity of the reaction allows the presence of various functionalities and in the case of carbonate derivatives, the nature of the final product was modulated by kinetic control, giving selectively hydroxyamides or cyclic carbamates. |
| Databáze: | OpenAIRE |
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