Département de chimie moléculaire

A review. The Baldwin rearrangement is a thermally induced ring contraction of 4-isoxazolines into 2-acylaziridines. The reaction yields highly strained nitrogen-contg. three-membered-ring compds. from readily available five-membered N-O heterocycles. Diversely substituted isoxazolines are directly transformed into a variety of highly functionalized 2-acylaziridines in a stereocontrolled process. In this review mechanistic aspects and stereoselectivity of this rearrangement are discussed. Although still undervalued, the Baldwin rearrangement may have significant applications in the synthesis of complex aziridine-contg. targets such as natural products or pharmaceuticals.