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: | , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2025 |
| País: | España |
| Institución: | Universidad Autónoma de Madrid |
| Repositorio: | Biblos-e Archivo. Repositorio Institucional de la UAM |
| Idioma: | inglés |
| OAI Identifier: | oai:repositorio.uam.es:10486/745920 |
| Acceso en línea: | https://hdl.handle.net/10486/745920 https://dx.doi.org/10.1021/jacs.5c15781 |
| Access Level: | acceso abierto |
| Palabra clave: | cyclopropane transition element electrophile Química |
| 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 intothe transmetalation/ring-opening sequence |
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