176696-39-2Relevant academic research and scientific papers
Stereospecific C-N bond cleavage of 4-silylated 1,2-thiazetidine 1,1- dioxides with EtAlCl2 or AlCl3: Formation of (E)-vinylsulfonamides
Iwama, Tetsuo,Takagi, Atsuko,Kataoka, Tadashi
, p. 757 - 766 (1998)
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.
