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

Abstract

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.