Aspects of the chemistry of 4-tributylstannyl-, 4-trimethylsilyl- and 2-phenylsulfinylallylstannanes

The 4-trimethylsilyl- and 4-tributylstannylbut-2-enyl(tributyl)stannanes 3 and 4 have been prepared by treatment of the allylic sulfones 6 and 7 with tributyltin hydride under free-radical conditions and shown to react under non-catalysed and Lewis acid promoted conditions with 4-nitrobenzaldehyde to give the anti- and syn-products 9/11 and 8/10, respectively, with reasonable levels of stereoselectivity. The 2-arylsulfinylpropenylstannanes 17 and 18 were also prepared from the sulfones 15 and 16, and found to undergo stereoselective titanium(IV) chloride promoted reactions with aldehydes.