Synthesis and reactivity of β-sulfonylvinylselenonium salts: a simple stereoselective synthesis of β-functionalized (Z )-vinyl sulfones
作者:Shin-ichi Watanabe、Keiichirou Yamamoto、Yukiko Itagaki、Tatsunori Iwamura、Tetsuo Iwama、Tadashi Kataoka、Genzoh Tanabe、Osamu Muraoka
DOI:10.1039/b007715l
日期:——
The treatment of alkynylselenonium salt with benzenesulfinic acid in iPrOH gives (Z)-β-sulfonylvinylselenonium salts in good yields. The alkenylselenonium salts thus prepared react with nucleophiles such as alkoxides, halides, and acetylides to produce β-functionalized (Z)-vinyl sulfones in high yields. Furthermore, we succeeded in the simple stereoselective one-step synthesis of various chiral (Z)-β-alkoxyvinyl sulfones by the use of chiral alcohols.
在 iPrOH 中用苯亚磺酸处理炔基硒鎓盐,可以得到收率很高的(Z)-δ-砜基乙烯基硒鎓盐。由此制备的烯基硒盐与亲核物(如烷氧基、卤化物和乙酰化物)发生反应,可高产率地生成δ-官能化的(Z)-乙烯基砜。此外,我们还利用手性醇成功地一步合成了各种手性 (Z)-δ²- 烷氧基乙烯基砜。