(2S,3S,S_S)-3-(α-naphthyl)-2-(p-tolylsulfinyl)oxirane | 1227009-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,3S,S_S)-3-(α-naphthyl)-2-(p-tolylsulfinyl)oxirane
• CAS: 1227009-62-2
• 化学式: C₁₉H₁₆O₂S
• 分子量: 308.401
• InChiKey: IEGFGVXCYDKFPE-IPJJNNNSSA-N

反应信息

• 作为产物：
  描述：

  (S)-dimethylsulfonium(p-tolylsulfinyl)methane tetrafluoroborate 、 1-萘甲醛 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R,S_S)-3-(α-naphthyl)-2-(p-tolylsulfinyl)oxirane 、 (2S,3S,S_S)-3-(α-naphthyl)-2-(p-tolylsulfinyl)oxirane
  参考文献：
  名称：

  Limitations, mechanism and understanding of the origins of stereocontrol in (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide-mediated epoxidation reactions

  摘要：

  The reaction of the (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide with aldehydes gave alpha,beta-epoxy sulfoxides with high enantioselectivity and diastereoselectivity dependent on the aldehyde. The mechanism of the 'model' reactions [ylide substituted with Me S(O) or Ph S(O) with MeCHO or PhCHO] has been studied in detail using density functional theory. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.012