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Synlett 1991; 1991(2): 101-104
DOI: 10.1055/s-1991-20642
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α-Sulfinyl Substituted Radicals; I. Stereoselective Radical Addition Reactions of Cyclic α-Sulfinyl Radicals1

Adrian Waldner* , Alain De Mesmaeker, Pascale Hoffmann, Thomas Mindt, Tammo Winkler
  • *Central Research Laboratories, Ciba-Geigy Ltd., CH-4002 Basel, Switzerland
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Publication Date:
07 March 2002 (online)

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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.

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