Palladium-Catalyzed Stereoselective Hydrostannation of Substituted Propargyl Alcohols with Trineophyltin Hydride

M. BELÉN FARAONI; DARÍO C. GERBINO; JULIO C. PODESTÁ

JOURNAL OF ORGANOMETALLIC CHEMISTRY

Elsevier

Lugar: South Carolina, Columbia, USA; Año: 2008 vol. 693 p. 1877 - 1885

0022-328X

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 a/b regioselectivity might be ascribed to the steric bulk of the proximal substituents rather than to electronic effects. Full took place in good to excellent yields and, mostly, with a high degree of stereoselectivity. The results obtained suggest that the observed a/b regioselectivity might be ascribed to the steric bulk of the proximal substituents rather than to electronic effects. Full 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 a/b regioselectivity might be ascribed to the steric bulk of the proximal substituents rather than to electronic effects. Full took place in good to excellent yields and, mostly, with a high degree of stereoselectivity. The results obtained suggest that the observed a/b regioselectivity might be ascribed to the steric bulk of the proximal substituents rather than to electronic effects. Full 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 a/b regioselectivity might be ascribed to the steric bulk of the proximal substituents rather than to electronic effects. Full took place in good to excellent yields and, mostly, with a high degree of stereoselectivity. The results obtained suggest that the observed a/b regioselectivity might be ascribed to the steric bulk of the proximal substituents rather than to electronic effects. Full 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 a/b regioselectivity might be ascribed to the steric bulk of the proximal substituents rather than to electronic effects. Fulla/b 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.H-, 13C-, and 119Sn NMR characteristics are included. 2008 Elsevier B.V. All rights reserved.2008 Elsevier B.V. All rights reserved. Keywords: Hydrostannation; Palladium catalyzed; Stereoselectivity; Propargyl alcohols; Stannylated allyl alcoholsHydrostannation; Palladium catalyzed; Stereoselectivity; Propargyl alcohols; Stannylated allyl alcohols