α-Sulfinyl Substituted Radicals; I. Stereoselective Radical Addition Reactions of Cyclic α-Sulfinyl Radicals1

All articles of this category Enantiomerically pure 3-oxo-2-(1-phenylethyl)-5-isothiazolidinyl 1-oxide radicals, prepared from the corresponding 5-phenylseleno compound, undergo addition reactions with (2-alkenyl)tributyltin derivatives to give 5-(2-alkenyl)-2-(1-phenylethyl)-3-isothiazolidone 1-oxides with good to excellent diastereoselectivity. The steric discrimination of the diastereotopic faces of the α-sulfinyl radical occurs between the sulfinyl oxygen and the sulfur lone pair. Moreover, it was found that the diastereoselectivity of these radical addition reactions is strongly solvent dependent.