Reduction of propargylic sulfones to (Z)-allylic sulfones using zinc and ammonium chloride

Propargylic sulfones can be cis-hydrogenated using commercial zinc powder and ammonium chloride in THF–water at room temperature, the major products being the corresponding (Z)-allylic sulfones. Other reducible groups (alkene, benzyloxy) are not affected. Allenylsulfones are implicated in one of the possible reaction pathways.