Stereospecific C-N Bond Cleavage of 4-Silylated 1,2-Thiazetidine 1,1-Dioxides with EtAlCl_2 or AlCl_3 : Formation of (E)-Vinylsulfonamides

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概要

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• Monosilylation of 1,2-thiazetidine 1,1-dioxides (β-sultams) 3 gave (3R^*, 4S^*)-4-monosilyl-β-sultams 4 stereoselectively. Disilylated β-sultams 5 were obtained by the use of trimethylsilyl chloride. Treatment of 4-monosilyl-β-sultams 4 with EtAlCl_2 caused stereospecific C-N bond cleavage owing to β-cation stabilization of the silicon group to provide (E)-vinylsulfonamides (E)-7. (E)-α-Silylstyrylsulfonamides (E)-7j-l were generated in the reaction of 4,4-disilyl-β-sultams 5 with EtAlCl_2. Reaction of 4-silyl-β-sultams with AlCl_3 afforded N-dealkylated (E)-vinylsulfonamides in good yields. Reaction of (E)-α-silylstyrylsulfonamide (E)-10 with benzaldehyde in the presence of tetrabutylammonium fluoride and BF_3・Et_2O provided the allylic alcohol (E)-12.

• 公益社団法人日本薬学会の論文
• 1998-05-15

著者

• Iwama Tetsuo

  Gifu Pharmaceutical University

• KATAOKA Tadashi

  Gifu Pharmaceutical University

• TAKAGI Atsuko

  Gifu Pharmaceutical University

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