1,3 acyclic control in free radical reactions: Threo—selective additions

Summary Oxazolidinone acrylamides undergo addition reactions with alkyl iodides and allyltributylstannane to give 1,3-substituted products with a threo preference in excess of 10:1. This threo preference is highest for reactions carried out in nonpolar solvents, a result consistent with dipolar stabilization of the transition state leading to the threo product.