2-ethyl 3,4-dimethyl (2R,3S,4R,5S)-5-(4-chlorophenyl)pyrrolidine-2,3,4-tricarboxylate

• 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-ethyl 3,4-dimethyl (2R,3S,4R,5S)-5-(4-chlorophenyl)pyrrolidine-2,3,4-tricarboxylate
• 英文别名: (2R,3S,4R,5S)-2-carboethoxy-3,4-dicarbomethoxy-5-(4-chlorophenyl)pyrrolidine；2-O-ethyl 3-O,4-O-dimethyl (2R,3S,4R,5S)-5-(4-chlorophenyl)pyrrolidine-2,3,4-tricarboxylate
• 化学式: C₁₇H₂₀ClNO₆
• 分子量: 369.802
• InChiKey: GKTITCQIFYQAEN-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 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：

  N-(4-chlorophenyl)methyleneglycine ethyl ester 、 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， 以94%的产率得到2-ethyl 3,4-dimethyl (2R,3S,4R,5S)-5-(4-chlorophenyl)pyrrolidine-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

• AgOAc catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with chiral ferrocene derived P,S ligands
  作者：Wei Zeng、Yong-Gui Zhou

  DOI：10.1016/j.tetlet.2007.04.101

  日期：2007.6

  Ferrocene derived P,S-heterodonor ligands were effectively used in AgOAc catalyzed asymmetric cycloaddition of azomethine ylides. The roles of planar chirality and electronic properties of the phosphorous substituents have been examined, and up to 93% ee was obtained.

  二茂铁衍生的P，S-杂配体配体可有效地用于AgOAc催化的甲亚胺基团的不对称环加成反应。已经检查了磷取代基的平面手性和电子性质的作用，并且获得了高达93％的ee。
• Hydrogen-Bonding Directed Reversal of Enantioselectivity
  作者：Wei Zeng、Guo-Ying Chen、Yong-Gui Zhou、Yu-Xue Li

  DOI：10.1021/ja067346f

  日期：2007.1.1

  successful stereochemical reversal was achieved in AgOAc catalyzed [3+2] cycloaddition by the formation of hydrogen bonding between ligand and reactant. This strategy provides an efficient and convenient route to prepare both enantiomers of a chiral compound. DFT studies proposed a reasonable mechanism of the reversal of the enantioselectivity; hydrogen bonding changed the transition state. The strategy

  通过在配体和反应物之间形成氢键，在 AgOAc 催化的 [3+2] 环加成反应中实现了成功的立体化学逆转。该策略提供了一种有效且方便的途径来制备手性化合物的两种对映异构体。DFT 研究提出了对映选择性逆转的合理机制；氢键改变了过渡态。该策略可为配体设计提供一些有用的提示。
• Synthesis of new chiral ferrocenyl P,N-ligands with a benzoxazole ring and their application in Ag-catalyzed asymmetric [3+2] cycloaddition
  作者：Sheng Yan、Cheng Zhang、Ya-Hui Wang、Zhong Cao、Zhuo Zheng、Xiang-Ping Hu

  DOI：10.1016/j.tetlet.2013.05.003

  日期：2013.7

  New chiral ferrocenyl P,N-ligands with a benzoxazole ring as the N-donor group have been synthesized from 2-aminophenol through a three-step transformation and successfully employed in the Ag-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with electron-deficient alkenes. High diastereoselectivities, excellent enantioselectivities, and good yields have been achieved for a variety of substrates, demonstrating the potential of these new P,N-ligands in asymmetric catalysis. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.