Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride

Authors
Faraoni, María Belén; Gerbino, Darío César; Podestá, Julio Cesar
Publication Year
2008
Language
English
Format
article
Status
Published version
Description
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.
Fil: Faraoni, María Belén. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Subject
HYDROSTANNATION
PALLADIUM CATALYZED
PROPARGYL ALCOHOLS
STANNYLATED ALLYL ALCOHOLS
STEREOSELECTIVITY
Otras Ciencias Químicas
Ciencias Químicas
CIENCIAS NATURALES Y EXACTAS
Access level
Restricted access
License
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repository
CONICET Digital (CONICET)
Institution
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identifier
oai:ri.conicet.gov.ar:11336/66020