trimethyl (2S,3R,4S,5R)-5-(4-nitrophenyl)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: trimethyl (2S,3R,4S,5R)-5-(4-nitrophenyl)pyrrolidine-2,3,4-tricarboxylate
• 化学式: C₁₆H₁₈N₂O₈
• 分子量: 366.328
• InChiKey: ACOBIRHRNKBZAG-RNJOBUHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  马来酸二甲酯 在 lead(IV) acetate 、 盐酸 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 56.17h， 生成 trimethyl (2S,3R,4S,5R)-5-(4-nitrophenyl)pyrrolidine-2,3,4-tricarboxylate
  参考文献：
  名称：

  Asymmetric [1,3]-dipolar cycloaddition reactions: synthesis of highly substituted proline derivatives

  摘要：

  The asymmetric [1,3]-dipolar cycloaddition reactions of azomethine ylides derived from (5R,6S)-2,3,5,6-tetrahydro-5,6-diphenyl-1,4-oxazin-2-one with various aldehydes and dimethyl maleate is described. The reactions prove to be highly endo-selective, installing three contiguous stereogenic centers in the newly formed five-membered ring with essentially complete stereochemical control. In the case of aldehydes higher than formaldehyde, a fourth stereogenic center is created; in most cases, poor stereoselectivity is observed at this center; the diastereomers formed in these cases can be separated by chromatography and separately converted into the amino acids. The bicyclic dipolar adducts can be cleaved with either catalytic hydrogenolysis or hydrolytic ring opening, esterification, and lead tetraacetate removal of the chiral auxiliary.

  DOI：

  10.1021/jo00050a029

文献信息

• Chiral ferrocenyl P,S-ligands for highly efficient copper-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides
  作者：Fu-Zhong Han、Sai-Bo Yu、Cheng Zhang、Xiang-Ping Hu

  DOI：10.1016/j.tet.2015.01.003

  日期：2016.5

  on benzimidazole and imidazole backbones have been prepared from Ugi's amine through a three-step transformation. These ligands were successfully employed in the Cu-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with various electron-deficient olefins, giving the corresponding cycloadducts in high endo-selectivities and excellent enantioselectivities (up to 99% ee).

  通过三步转化，由乌吉的胺制备了一系列基于苯并咪唑和咪唑骨架的手性二茂铁基P，S-配体。这些配体已成功地用于铜催化的偶氮甲亚胺与各种缺电子的烯烃的不对称[3 + 2]环加成中，从而以较高的内选择性和出色的对映选择性（高达99％ee）得到相应的环加合物。
• New chiral ferrocenyl P,S-ligands for highly diastereo- and enantioselective Ag(I)-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides
  作者：Mei-Ling Han、Dao-Yong Wang、Pei-Wei Zeng、Zhuo Zheng、Xiang-Ping Hu

  DOI：10.1016/j.tetasy.2012.02.017

  日期：2012.2

  A new family of chiral ferrocenyl P,S-ligands incorporating an indole ring at the alpha-ferrocenylmethyl position has been prepared via a Friedel-Crafts alkylation reaction of (R-c,S-Fc)-PPFA with a variety of 2-indole thioethers. These newly developed ferrocenyl P,S-ligands proved to be efficient in the AgOAc-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with various dipolarophiles, giving cycloadducts with high diastereoselectivities and enantioselectivities (up to 99% ee). (C) 2012 Elsevier Ltd. All rights reserved.
• Asymmetric [1,3]-dipolar cycloaddition reactions: synthesis of highly substituted proline derivatives
  作者：Robert M. Williams、Weixu Zhai、David J. Aldous、Suzanne C. Aldous

  DOI：10.1021/jo00050a029

  日期：1992.11

  The asymmetric [1,3]-dipolar cycloaddition reactions of azomethine ylides derived from (5R,6S)-2,3,5,6-tetrahydro-5,6-diphenyl-1,4-oxazin-2-one with various aldehydes and dimethyl maleate is described. The reactions prove to be highly endo-selective, installing three contiguous stereogenic centers in the newly formed five-membered ring with essentially complete stereochemical control. In the case of aldehydes higher than formaldehyde, a fourth stereogenic center is created; in most cases, poor stereoselectivity is observed at this center; the diastereomers formed in these cases can be separated by chromatography and separately converted into the amino acids. The bicyclic dipolar adducts can be cleaved with either catalytic hydrogenolysis or hydrolytic ring opening, esterification, and lead tetraacetate removal of the chiral auxiliary.