Cyclopropylmethyl Boronic Esters as General Reagents in Transition-Metal Catalyzed Homoallylation Reactions
Herein we disclose the use of cyclopropylmethyl boronates as general reagents in Negishi-type homoallylation reactions. This strategy provides a novel approach to generate enantioenriched homoallyl-Zn species through boron-to-zinc transmetalation. Subsequent sp2–sp3 cross-coupling offers a platform...
| Autores: | , , , |
|---|---|
| Tipo de recurso: | artículo |
| Fecha de publicación: | 2025 |
| País: | España |
| Institución: | Universidad Complutense de Madrid (UCM) |
| Repositorio: | Docta Complutense |
| Idioma: | inglés |
| OAI Identifier: | oai:docta.ucm.es:20.500.14352/131542 |
| Acceso en línea: | https://hdl.handle.net/20.500.14352/131542 |
| Access Level: | acceso abierto |
| Palabra clave: | 547 Aldehydes Cross coupling reaction Hydrocarbons Organic compounds Reagents Química orgánica (Química) 2306 Química Orgánica |
| Sumario: | Herein we disclose the use of cyclopropylmethyl boronates as general reagents in Negishi-type homoallylation reactions. This strategy provides a novel approach to generate enantioenriched homoallyl-Zn species through boron-to-zinc transmetalation. Subsequent sp2–sp3 cross-coupling offers a platform for the preparation of arenes, ketones, and 1,5-dienes containing a chiral homoallylic scaffold. The method has been applied to the late-stage functionalization of known drugs and the preparation of precursors of biologically relevant compounds. Mechanistic experiments and DFT calculations provide insight into the transmetalation/ring-opening sequence. |
|---|