ISOTHIAZOLE 1,1-DIOXIDES - FROM SWEETER T O CHIRAL AUXILIAR IN THE STEREOSELECTIVE SYNTHESIS

This review gives a report of the last ten years on the new synthetic methods, reactions and biological applications of isothiazole 1,1-diox ide derivatives. The formation of monocyclic and heterocyclic annelate d isothiazole 1,1-dioxides by oxidation of isothiazoles, cyclocondensa tion of sulfonamides and cycloaddition of isothiazol-3 (2H)-one 1,1-di oxides are discussed in more detail. Furthermore, the preparation of p harmacologically important N-substituted saccharines is reported. New saccharine-derived chiral N-enoyl- and N-acyl-2,3-dihydro-1,2-benzisot hiazole 1,1-dioxides serve as advantageous stereoface-directing dienop hile and dipolarophile auxiliaries in Diels-Alder-reactions and 1,3-di polar cycloadditions. Asymmetric alkylations, acylations and aldolizat ions are also described.