methyl (1S,3S,3aS,6aR)-5-ethyl-3a-methyl-3-phenyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate | 1140972-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl (1S,3S,3aS,6aR)-5-ethyl-3a-methyl-3-phenyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• CAS: 1140972-18-4
• 化学式: C₁₇H₂₀N₂O₄
• 分子量: 316.357
• InChiKey: YPDPMHQBXKBWIF-XREXNNHRSA-N

物化性质

• 沸点：
  468.4±45.0 °C(predicted)
• 密度：
  1.230±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为产物：
  描述：

  N-Ethyl-2-methyl-maleinimid 、 methyl benzylideneiminoglycinate 在 silver perchlorate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 methyl (1R,3S,3aR,6aS)-5-ethyl-6a-methyl-3-phenyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate 、 methyl (1S,3R,3aS,6aR)-5-ethyl-6a-methyl-3-phenyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate 、 methyl (1S,3S,3aS,6aR)-5-ethyl-3a-methyl-3-phenyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate 、 methyl (1R,3R,3aR,6aS)-5-ethyl-3a-methyl-3-phenyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of polysubstituted prolines by Binap-silver-catalyzed 1,3-dipolar cycloadditions

  摘要：

  The enantioselective 1,3-dipolar cycloaddition reaction of stabilized azomethine ylides, generated from iminoesters, with maleimides was efficiently achieved by intermediacy of an equimolar mixture of chiral (R)- or (S)-Binap and AgClO4. The high stability of the titled catalytic metal-complex to light exposure and its insolubility in toluene made possible its recovery and reutilization in other new process. In order to get a better understanding of the behavior of these chiral catalysts, we have carried out DFT1 calculations demonstrating the experimentally observed high enantio- and endo-selectivity through a very asynchronous transition state. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.021