This Concept article summarises recent advances in approaches to the synthesis of important vinyl stannane building blocks in a stereocontrolled and regiocontrolled manner. Particular emphasis is put on those routes in which judicious choice of ligand affords a switchable reaction, providing routes to stereodefined olefins from a single starting material.

Abstract

Organostannanes have represented one of the most widely applied reagents in modern cross-coupling chemistry and represent a key reagent in the synthesis of a range of pharmaceutically relevant scaffolds. This Concept article reviews recent advances in approaches to the synthesis of these building blocks in a stereocontrolled and regiocontrolled manner. Particular focus is paid to methods which allow for divergent synthesis of alkenylstannanes and developments in methods which present opportunities for sustainable synthesis.