1,3-Diastereocontrol in acyclic radical allylations

The radical allylation of an acyclic α-hydroxyketone with allyltributyltin under chelation-controlled conditions is reported. Several reaction conditions were explored, including radical initiators, solvents, and temperatures to improve the yield and the diastereomeric ratio. Some Lewis acids, like magnesium bromide etherate and zinc chloride, gave superior diastereomeric ratios (up to 100:1) and good yields.