α-Functionalisation of Cyclic Sulfides Enabled by Lithiation Trapping

A general and straightforward procedure for the lithiation trapping of cyclic sulfides such as tetrahydrothiophene, tetrahydrothiopyran and a thiomorpholine is described. Trapping with a wide range of electrophiles is demonstrated, leading to more than 50 diverse alpha-substituted saturated sulfur heterocycles. The methodology provides access to a range of alpha-substituted cyclic sulfides that are not easily synthesised by the currently available methods.

Automated summary

This study describes a general and straightforward procedure for the lithiation trapping of cyclic sulfides. By trapping with various electrophiles, over 50 diverse alpha-substituted saturated sulfur heterocycles are successfully synthesized. This method provides access to alpha-substituted cyclic sulfides that are not easily synthesized by currently available methods.