Chemical and Pharmaceutical Bulletin p. 757 - 766 (1998)
Update date:2022-08-04
Topics:
Iwama, Tetsuo
Takagi, Atsuko
Kataoka, Tadashi
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 EtAlCl2 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 EtAlCl2. Reaction of 4-silyl-β-sultams with AlCl3 afforded N-dealkylated (E)- vinylsulfonamides in good yields. Reaction of (E)-α-silylstyrylsulfonamide (E)-10 with benzaldehyde in the presence of tetrabutylammonium fluoride and BF3·Et2O provided the allylic alcohol (E)-12.
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