dimethyl (2R,3R)-2-hydroxy-3-(nitrooxy)succinate | 13171-65-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: dimethyl (2R,3R)-2-hydroxy-3-(nitrooxy)succinate
• 英文别名: (2R,3R)-2-Hydroxy-3-nitrooxy-succinic acid dimethyl ester
• CAS: 13171-65-8
• 化学式: C₆H₉NO₈
• 分子量: 223.139
• InChiKey: WJUHTBVOLGXSKQ-QWWZWVQMSA-N

反应信息

• 作为产物：
  描述：

  L-(+)-酒石酸二甲酯 在 6-nitro-N-nitrosaccharin 作用下， 以 乙腈 为溶剂， 以81 %的产率得到dimethyl (2R,3R)-2-hydroxy-3-(nitrooxy)succinate
  参考文献：
  名称：

  Overcoming Challenges in O‐Nitration: Selective Alcohol Nitration Deploying N,6‐Dinitrosaccharin and Lewis Acid Catalysis

  摘要：

  Nitrate esters hold pivotal roles in pharmaceuticals, energetic materials, and atmospheric processes, motivating the development of efficient synthesis routes. Here, we present a novel catalytic method for the synthesis of nitrates via the direct O‐nitration of alcohols, addressing limitations of current traditional methods. Leveraging bench‐stable and recoverable N,6‐dinitrosaccharin reagent, our catalytic strategy employs magnesium triflate to achieve mild and selective O‐nitration of alcohols, offering broad substrate scope and unprecedented large functional group tolerance (e.g. alkenes, alkynes, carbonyls). DFT mechanistic studies reveal a dual role of the magnesium catalyst in the activation of both the nitrating reagent and the alcohol substrate. They also unveil a barrierless proton transfer upon formation of a widely‐accepted — yet elusive in solution — nitrooxonium ion intermediate. Overall, our work contributes to the development of mild, selective, and sustainable approaches to nitrates synthesis, with potential applications in drug discovery, materials science, and environmental chemistry.

  DOI：

  10.1002/anie.202411073