γ-Lactam synthesis from cyclobutanone via transoximation and the Beckmann rearrangement

Abstract

This manuscript describes the synthesis of γ-lactam from the nitrogen insertion reaction of cyclobutanones using an oxime as an aminating reagent with a catalytic amount of Brønsted acid. This method was employed with a more stable oxime reagent, which is a precursor analog of hydroxylamine derivatives with explosive properties. The reaction was tolerated by various substituted cyclobutanones and less strained five- or six-membered ketones. The obtained γ-lactam products could be transformed into γ-aminobutyric acid derivatives via ring-opening hydrolysis. The reaction mechanism is discussed from the perspective of the isotope effect, etc.