tert-butyl (1S,3R,3aS,6aR)-5-methyl-3-(2-naphthyl)-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate | 1140972-13-9

• 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: tert-butyl (1S,3R,3aS,6aR)-5-methyl-3-(2-naphthyl)-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• CAS: 1140972-13-9
• 化学式: C₂₂H₂₄N₂O₄
• 分子量: 380.444
• InChiKey: BSFVTKUWVHPYLN-MHORFTMASA-N

物化性质

• 熔点：
  150-152 °C
• 沸点：
  560.0±50.0 °C(predicted)
• 密度：
  1.233±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为产物：
  描述：

  N-甲基马来酰亚胺 、 在 silver perchlorate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成 tert-butyl (1S,3R,3aS,6aR)-5-methyl-3-(2-naphthyl)-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate 、 tert-butyl (1RS,3SR,3aSR,6aRS)-5-methyl-3-(2-naphthyl)-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