(1S,3aS,6aR)-methyl 4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate

• 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: (1S,3aS,6aR)-methyl 4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• 英文别名: methyl (3S,3aR,6aS)-4,6-dioxo-5-phenyl-3a,6a-dihydro-3H-pyrrolo[3,4-c]pyrrole-3-carboxylate
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: LYXQTJYGSKJZGI-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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 、 异腈基乙酸甲酯 在 silver hexafluoroantimonate 、 (R)-DTBM-segphos(AuCl)2 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (1S,3aS,6aR)-methyl 4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate 、 (1R,3aR,6aS)-methyl 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

• Silver acetate catalysed cycloadditions of isocyanoacetates
  作者：Ronald Grigg、Mark I. Lansdell、Mark Thornton-Pett

  DOI：10.1016/s0040-4020(98)01216-2

  日期：1999.2

  Silver acetate is an efficient catalyst for the cycloaddition of methyl isocyanoacetate with Michael-acceptors under mild conditions to give Δ1- or Δ2-pyrrolines in good yields. In the case of acrolein, novel chemoselectivity was observed. In the absence of a suitable olefin isocyanoacetates undergo silver acetate catalysed cyclodimerisation to give imidazoles in excellent yields. The mechanism of

  醋酸银是用于与迈克尔受体异氰基乙酸甲酯的温和条件下环合加成，得到一种有效的催化剂Δ 1 -或Δ 2个以良好的收率-pyrrolines。在丙烯醛的情况下，观察到新的化学选择性。在不存在合适的烯烃的情况下，异氰基乙酸酯经历乙酸银催化的环二聚反应，以优异的产率得到咪唑。已经探讨了环加成的机理。该反应已通过一锅顺序级联过程与甲亚胺叶立德1，3-偶极环加成反应结合，以提供7-氮杂双环[2.2.1]庚烷环系，这是自然有效的强效镇痛依帕替丁的特征结构特征。
• 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.