Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride
This paper reports results obtained in a study on the palladium-catalyzed hydrostannation of substituted propargyl alcohols with the bulky trineophyltin hydride (1). The reaction of 1 with 10 propargyl alcohols containing one up to three substituents, was carried out in THF at room temperature leadi...
| Autores: | , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2008 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/66020 |
| Acceso en línea: | http://hdl.handle.net/11336/66020 |
| Access Level: | acceso abierto |
| Palabra clave: | Hydrostannation Palladium Catalyzed Propargyl Alcohols Stannylated Allyl Alcohols Stereoselectivity https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Sumario: | This paper reports results obtained in a study on the palladium-catalyzed hydrostannation of substituted propargyl alcohols with the bulky trineophyltin hydride (1). The reaction of 1 with 10 propargyl alcohols containing one up to three substituents, was carried out in THF at room temperature leading to the corresponding allylstannanes following in all cases a syn addition stereochemistry. These additions took place in good to excellent yields and, mostly, with a high degree of stereoselectivity. The results obtained suggest that the observed α/β regioselectivity might be ascribed to the steric bulk of the proximal substituents rather than to electronic effects. Full 1H-, 13C-, and 119Sn NMR characteristics are included. © 2008 Elsevier B.V. All rights reserved. |
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