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Synlett 1993; 1993(7): 481-482
DOI: 10.1055/s-1993-22498
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Synthesis of E-N-Unfunctionalized α,β-Unsaturated Sulfoximines and N-Trifluoromethanesulfonyl Derivatives

Donald Craig* , Neil J. Geach
  • *Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, England
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Publication Date:
19 March 2002 (online)

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Sequential treatment of the lithio-anion of S -methyl-S-phenyl-N-(trimethylsilyl)sulfoximine 1 with aldehydes and methyl chloroformate gives crude N-(trimethylsilyl)-β-methoxycarbonyl-oxysulfoximines 2, which upon exposure to potassium tert-butoxide and acidic work-up yield geometrically pure N -unfunctionalized α,β-unsaturated sulfoximines 3. Reaction of 3 with trifluoromethanesulfonic anhydride and pyridine gives the N-trifluoromethanesulfonyl derivatives 4.