Stereospecific C-N Bond Cleavage of 4-Silylated 1,2-Thiazetidine 1,1-Dioxides with EtAlCl2 or AlCl3: Formation of (E)-Vinylsulfonamides.
書誌事項
- タイトル別名
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- Stereospecific C N Bond Cleavage of 4 S
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抄録
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.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 46 (5), 757-766, 1998
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390282679136573568
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- NII論文ID
- 130003947598
- 110003662860
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 4486182
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
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- 使用不可