Stille Coupling of α-Acyloxybenzylstannanes with Acid Chlorides

Abstract

Two widely-accepted models (open- and cyclic- transmetalation) are applied to explain the stereochemical outcome of the Stille coupling with organotin compounds containing an sp3 chiral center. However, it is still not possible to predict the stereochemical outcome of this type of Stille coupling before the reaction is conducted. To have a better understanding of the detailed mechanism involved, the Stille couplings of different α-acyloxybenzylstannanes with different acid chlorides were studied in this project.