Stereospecific formation of deuterated homoallyl alcohols by Lewis acid-promoted reactions of allyltin and allylsilicon reagents toward aldehydes

Stereoselectively prepared (Z)-3-deuterioallyltin and (E)-3-deuterioallylsilicon were allowed to react with aldehydes in the presence of BF3·OEt2. The stereospecifically afforded products were predominantly an anti-homoallyl alcohol from the (Z)-reagent and a syn-one from the (E)-reagent. These results strongly indicate both reactions proceed via a syn-synclinal transition state.