Synthesis of 4-Nitrophenyl Sulfones and Application in the Modified Julia Olefination
作者:Jieping Zhu、Daniela Mirk、Jean-Marie Grassot
DOI:10.1055/s-2006-939682
日期:——
4-Nitrophenyl (NP) sulfones were successfully employed in the modified Julia olefination reaction with carbonyl compds. The olefination reaction proceeds through a sequence of aldol addn., Smiles rearrangement, and elimination. The sulfones are easily prepd. in high yields in a two-step sequence starting from inexpensive com. available para-fluoronitrobenzenes via nucleophilic arom. substitution by
4-硝基苯基 (NP) 砜成功地用于与羰基化合物的改性 Julia 烯化反应。烯化反应通过羟醛加成、Smiles 重排和消除的顺序进行。砜很容易制备。从廉价的 com 开始,以两步顺序高产。可通过亲核芳族获得对氟硝基苯。被硫醇取代,随后被氧化。在标准下。使适应。NP 砜与多种芳烃之间的改良 Julia 反应。醛提供相应的苯乙烯、芪和肉桂酸酯衍生物。产率 ?97% 和良好的立体选择性。提出了机械原理来解释 obsd。结果。[在 SciFinder (R) 上]