3-bromozinc propenyl esters: an experimental and theoretical study of the unique stereocrossover observed in their addition to aromatic and aliphatic aldehydes

A combination of experimental and theoretical study results for the reaction of 3-bromopropenyl acetate in the presence of zinc with three different aldehydes are reported. The studies provide insight into structural features of adducts with phenyl ring and the acetate group placed on almost parallel planes which favors stabilizing [pi]-stacking interactions.