trimethyl (2S,3R,4S,5R)-5-(3-nitrophenyl)pyrrolidine-2,3,4-tricarboxylate | 1373444-82-6

• 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-(3-nitrophenyl)pyrrolidine-2,3,4-tricarboxylate
• CAS: 1373444-82-6
• 化学式: C₁₆H₁₈N₂O₈
• 分子量: 366.328
• InChiKey: VGGUQJUINJJMLL-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：

  Methyl 2-[(3-nitrophenyl)methylideneamino]acetate 、 马来酸二甲酯 在 3-{(S)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyl}-2-(phenylthio)indole 、 silver(I) acetate 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 18.0h， 以93%的产率得到trimethyl (2S,3R,4S,5R)-5-(3-nitrophenyl)pyrrolidine-2,3,4-tricarboxylate
  参考文献：
  名称：

  New chiral ferrocenyl P,S-ligands for highly diastereo- and enantioselective Ag(I)-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2012.02.017

文献信息

• 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.