A Novel Stereoselective Preparation of Various Vinyl Sulfide Derivatives Using β-Alkylthioalkenylselenonium Salts
作者:Shin-ichi Watanabe、Eiji Mori、Hirotada Nagai、Tatsunori Iwamura、Tetsuo Iwama、Tadashi Kataoka
DOI:10.1021/jo000640k
日期:2000.12.1
The treatment of alkynylselenonium salt and various thiophenol derivatives with a catalytic amount of triethylamine gave beta-arylthioalkenylselenonium salts in good yields. The alkenylselenonium salts thus prepared reacted with nucleophiles such as acetylides, thiolates, and alkoxides to produce (Z)-beta-arylthio-alpha-functionalized ethenes in high yields. The vinylselenonium salts bearing a hydroxy
用催化量的三乙胺处理炔基硒鎓盐和各种硫酚衍生物,以良好的收率得到β-芳基硫基烯基硒鎓盐。如此制备的烯基硒鎓盐与亲核试剂如乙炔化物,硫醇盐和醇盐反应,以高收率生产(Z)-β-芳硫基-α-官能化的乙烯。在β侧链上带有羟基的乙烯基硒鎓盐在用氢化钠处理后产生分子内环化反应,从而生成含有硫和氧原子的中元杂环化合物。给出(Z)-β-芳硫基-α-官能化的乙烯的反应将通过形成亚硒酸酯中间体进行,然后进行配体偶联反应。