Download PDF
Synlett 1991; 1991(2): 101-104
DOI: 10.1055/s-1991-20642
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
07 March 2002 (online)

  PDF Download  Permissions and Reprints 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.