(1S,3aR,6aS)-methyl 4,6-dioxo-5-phenyl-1-(m-tolyl)-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate | 1372866-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (1S,3aR,6aS)-methyl 4,6-dioxo-5-phenyl-1-(m-tolyl)-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• 英文别名: methyl (3S,3aS,6aR)-3-(3-methylphenyl)-4,6-dioxo-5-phenyl-3a,6a-dihydropyrrolo[3,4-c]pyrrole-3-carboxylate
• CAS: 1372866-11-9
• 化学式: C₂₁H₁₈N₂O₄
• 分子量: 362.385
• InChiKey: NAKAAQNGNOVVKE-CSODHUTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  methyl 2-formamido-2-m-tolylacetate 在 silver hexafluoroantimonate 、 (R)-DTBM-segphos(AuCl) 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 (1R,3aS,6aR)-methyl 4,6-dioxo-5-phenyl-1-(m-tolyl)-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate 、 (1S,3aR,6aS)-methyl 4,6-dioxo-5-phenyl-1-(m-tolyl)-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

• Asymmetric Formal [3+2] Cycloaddition Reaction of α-Aryl Isocyanoesters with<i>N</i>-Aryl Maleimides by Bifunctional Cinchona Alkaloids-Based Squaramide/AgSbF₆Cooperative Catalysis
  作者：Mei-Xin Zhao、Deng-Ke Wei、Fei-Hu Ji、Xiao-Li Zhao、Min Shi

  DOI：10.1002/asia.201200686

  日期：2012.12

  better to be cooperative: A highly diastereo‐ and enantioselective asymmetric [3+2] cycloaddition reaction of α‐aryl isocyanoacetates with N‐aryl maleimides through cooperative catalysis of cinchona alkaloid‐derived squaramide/AgSbF6 was developed. A wide range of optically active, substituted 1,3a,4,5,6,6a‐hexahydropyrrolo[3,4‐c] pyrrole derivatives was obtained in high yields (up to 98 %), high diastereoselectivities

  最好是协同作用：通过金鸡纳生物碱衍生的方酸酰胺/ AgSbF 6的协同催化，开发了α-芳基异氰基乙酸酯与N-芳基马来酰亚胺的高度非对映体和对映选择性不对称[3 + 2]环加成反应。以高收率（高达98％），高非对映选择性（> 20：1 dr ），并且在温和的反应条件下对映体的选择性良好（高达ee的92％）。
• 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.