Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines
In the presence of 3-5 mol% Crabtree's catalyst or the corresponding tetrakis[3,5-bis(trifluoromethyl)phenyl]borate salt (Cy3P)Ir+(pyridine)(1,5-cyclooctadiene)·X- {X = PF6, [3,5-(F3C)2C6H3]4B}, aryl 1,1-disubstituted epoxides such as α-methylstyrene oxide underwent chemoselective isomerization...
| Autores: | , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2019 |
| País: | España |
| Institución: | Universidad de Barcelona |
| Repositorio: | Dipòsit Digital de la UB |
| OAI Identifier: | oai:diposit.ub.edu:2445/143377 |
| Acceso en línea: | https://hdl.handle.net/2445/143377 |
| Access Level: | acceso abierto |
| Palabra clave: | Iridi Isomerització Iridium Isomerization |
| Sumario: | In the presence of 3-5 mol% Crabtree's catalyst or the corresponding tetrakis[3,5-bis(trifluoromethyl)phenyl]borate salt (Cy3P)Ir+(pyridine)(1,5-cyclooctadiene)·X- {X = PF6, [3,5-(F3C)2C6H3]4B}, aryl 1,1-disubstituted epoxides such as α-methylstyrene oxide underwent chemoselective isomerization to aldehydes; treatment with benzhydrylamine and pyrrolidine and redn. with NaBH4 yielded 2,2-disubstituted amines such as PhCHMeCH2NHR [R = Ph2CH, 4-MeOC6H4, PhCH2, (R)-PhCHMe] in one pot. DFT calcns. were performed to rationalize the obsd. selectivity. |
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