We first examined the reaction of benzodioxole OSF 7 and (Cbz)ASF 14 reagents to form pomalidomide derivatives (Scheme 7b). Pomalidomide is commonly employed in degrader design but suffers from limited synthetic derivatization as a nucleophile due to the electron poor aniline and its low solubility in common organic solvents. Performing reactions under more dilute conditions (0.05 M acetonitrile) with slightly elevated temperature (80 °C) and pre-stirring facilitated greater dissolution in the reaction media. Subsequent addition of excess OSF or ASF led to effective formation of the desired amino-oxetane and azetidine in excellent yields (156, 157). Using OSF reagents 134 and 136