Efficient access to 3-substituted-γ-hydroxylactams: the uncatalyzed addition of diorganozinc reagents to cyclic imides with heterocyclic substitution

A range of 3-substituted-γ-hydroxylactams have been prepared via the uncatalyzed addition of organozinc nucleophiles to cyclic imides. This reactivity is primarily limited to imides containing heterocyclic N-substitution, but proceeds efficiently with a variety of diorganozinc reagents, including those prepared and utilized without purification, as well as organozinc halides. It is hypothesized that the presence of a Lewis basic directing group is required for optimum reactivity.