N-Alkylidenesulfinamides

Abstract

This review covers the preparation and reactions of racemic and chiral N-alkylidene-sulfinamides or sulfinimines, based on a CA search. Racemic sulfinimines have been prepared by imine formation of sulfinamides with ketones (only ketones containing electron-withdrawing groups react), oxidation of N-akylidenesulfenamides, and rearrangement of N-chlorosulfoximines. The chiral compounds have been prepared by addition of organomagnesium or organolithium reagents or of diisobutylaluminium hydride to nitriles, followed by l-menthyl (S)-p-toluenesulfinate, displacement reactions of lithium hexamethyldisilazide with l-menthyl (S)-p-toluenesulfinate, followed by CsF and aldehydes, asymmetric oxidation of N-alkylidenesulfenamides, and reactions of l-menthyl imidic esters with p-toluenesulfinyl chloride. Thermal fragmentations, nucleophilic addition reactions (attack at imino carbon) of N-alkylidenesulfinamides with various nucleophiles, and 1,3-dipolar cycloadditions illustrate the versatility of this functional group in organic synthesis.