(1R,3aR,6aS)-ethyl 1-benzyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate | 1372866-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1R,3aR,6aS)-ethyl 1-benzyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• 英文别名: ethyl (3R,3aS,6aR)-3-benzyl-4,6-dioxo-5-phenyl-3a,6a-dihydropyrrolo[3,4-c]pyrrole-3-carboxylate
• CAS: 1372866-14-2
• 化学式: C₂₂H₂₀N₂O₄
• 分子量: 376.412
• InChiKey: JPEXAJMLECZVOM-NJNPRVFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-苯基马来酰亚胺 、 methyl 2-isocyano-3-phenylpropanoate 在 silver hexafluoroantimonate 、 (R)-DTBM-segphos(AuCl) 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (1S,3aS,6aR)-ethyl 1-benzyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate 、 (1R,3aR,6aS)-ethyl 1-benzyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate
  参考文献：
  名称：

  Au-Catalyzed Asymmetric Formal [3 + 2] Cycloaddition of Isocyanoacetates with Maleimides

  摘要：

  An efficient protocol for the Au-I-catalyzed asymmetric formal [3 + 2] cycloaddition of isocyanoacetates with phenylmaleimide has been developed. In the presence of cationic Au-I/DTBM-segphos complex, excellent diastereoselectivity and high levels of enantioselectivity (up to 97% cc) have been attained with a variety of alpha-substituted isocyanoacetates. The synthetic potential of the resulting enantioenriched 1-pyrrolines has been demonstrated by the preparation of highly substituted pyrrolidines bearing a quaternary stereocenter.

  DOI：

  10.1021/jo3003425

文献信息

• Au-Catalyzed Asymmetric Formal [3 + 2] Cycloaddition of Isocyanoacetates with Maleimides
  作者：Silvia Padilla、Javier Adrio、Juan C. Carretero

  DOI：10.1021/jo3003425

  日期：2012.4.20

  An efficient protocol for the Au-I-catalyzed asymmetric formal [3 + 2] cycloaddition of isocyanoacetates with phenylmaleimide has been developed. In the presence of cationic Au-I/DTBM-segphos complex, excellent diastereoselectivity and high levels of enantioselectivity (up to 97% cc) have been attained with a variety of alpha-substituted isocyanoacetates. The synthetic potential of the resulting enantioenriched 1-pyrrolines has been demonstrated by the preparation of highly substituted pyrrolidines bearing a quaternary stereocenter.