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Synlett 1991; 1991(12): 913-915
DOI: 10.1055/s-1991-21988
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A New, One-Pot (E) -Stereoselective Synthesis of Racemic and Chiral α,β-Unsaturated Sulfoxides from Sulfinates and Lithium Dimethyldiphenylphosphonium Diylide

Marian Mikołajczyk* , Wiesława Perlikowska, Jan Omelańczuk, Henri-Jean Cristau, Anne Perraud-Darcy
  • *Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Organic Sulfur Compounds, PL-90-363 Łódź, Sienkiewicza 112, Poland
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Publication Date:
07 March 2002 (online)

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α,β-Unsaturated sulfoxides 6 with (E)-geometry, both racemic or optically active, were effectively synthesized by the one-pot reaction of lithium dimethyldiphenylphosphonium diylide [1; lithiomethyl(methylene)diphenylphosphorane] with sulfinates 2 followed by treatment of the α-sulfinylmethylmethyldiphenylphosphonium ylide formed [4; methyldiphenyl(sulfinylmethylene)-phosphorane] with aldehydes.