2-O-ethyl 3-O,4-O-dimethyl (2R,3S,4R,5S)-5-phenylpyrrolidine-2,3,4-tricarboxylate | 1166397-78-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-O-ethyl 3-O,4-O-dimethyl (2R,3S,4R,5S)-5-phenylpyrrolidine-2,3,4-tricarboxylate
• CAS: 1166397-78-9
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: PLFGGEUMFOHTJU-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ([1-苯基-meth-(e)-基idene]-氨基)-乙酸 乙酯 、 马来酸二甲酯 在 C₄₉H₃₉FeNO₂P₂ 、 silver(I) acetate 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 15.0h， 生成 、 2-O-ethyl 3-O,4-O-dimethyl (2R,3S,4R,5S)-5-phenylpyrrolidine-2,3,4-tricarboxylate
  参考文献：
  名称：

  Enantioselective Ag(I)-catalyzed [3+2] cycloaddition of azomethine ylides using a chiral ferrocene-based phosphine–phosphoramidite ligand having a stereogenic P-center

  摘要：

  A series of chiral ferrocene-based phosphine-phosphoramidite ligands (PPFAPhos) have been employed in the Ag(I)-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with dimethyl maleate. The results showed that the ligand with a stereogenic P-center in the phosphino moiety displayed the best diastereo- and enantioselectivities, in which LIP to 99% enantiomeric excesses and 99/1 endo/exo selectivities have been achieved. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.058

文献信息

• Acid-Base Dual-Functional Catalysis by Axially Chiral Guanidine in Enantioselective [3+2] Cycloaddition of Maleate to Schiff Bases as a Precursor of Azomethine Ylides
  作者：Masahiro Terada、Megumi Nakano

  DOI：10.1055/s-0029-1217345

  日期：——

  The enantioselective [3+2] cycloaddition reaction of dimethyl maleate with Schiff bases as the precursor of azomethine ylide was developed using axially chiral guanidine catalysts to provide optically active pyrrolidine derivatives. Acid-base dual-functional catalysis by an axially chiral guanidine through double hydrogen-bonding interaction is proposed to give the cycloaddition products in good yields.

  利用轴向手性胍催化剂，开发了马来酸二甲酯与作为氮丙啶亚甲基前体的席夫碱的[3+2]手性环加成反应，以提供具有光学活性的吡咯烷衍生物。通过双氢键相互作用，轴向手性胍的酸碱双功能催化可提高环加成产物的收率。
• Enantioselective Ag(I)-catalyzed [3+2] cycloaddition of azomethine ylides using a chiral ferrocene-based phosphine–phosphoramidite ligand having a stereogenic P-center
  作者：Sai-Bo Yu、Xiang-Ping Hu、Jun Deng、Dao-Yong Wang、Zheng-Chao Duan、Zhuo Zheng

  DOI：10.1016/j.tetasy.2009.02.058

  日期：2009.3

  A series of chiral ferrocene-based phosphine-phosphoramidite ligands (PPFAPhos) have been employed in the Ag(I)-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with dimethyl maleate. The results showed that the ligand with a stereogenic P-center in the phosphino moiety displayed the best diastereo- and enantioselectivities, in which LIP to 99% enantiomeric excesses and 99/1 endo/exo selectivities have been achieved. (C) 2009 Elsevier Ltd. All rights reserved.