(1S,3R,3aS,6aR)-methyl 4,6-dioxo-3-(3-bromophenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate | 939799-31-2

• 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,3R,3aS,6aR)-methyl 4,6-dioxo-3-(3-bromophenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• 英文别名: methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(m-bromophenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate；(-)-methyl 3-(3-bromophenyl)-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate；(+)-methyl 3-(3-bromophenyl)-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• CAS: 939799-31-2
• 化学式: C₂₀H₁₇BrN₂O₄
• 分子量: 429.27
• InChiKey: QUQSCUHQASNUHD-YVSFHVDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  N-苯基马来酰亚胺 、 methyl [(3-bromobenzylidene)amino]acetate 在 2-((1R)-((tert-butylsulfinyl)amino)(phenyl)methyl)-6-(diphenylphosphanyl)-N,N-diisopropylbenzamide 、 水 、 silver fluoride 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以85% ee的产率得到
  参考文献：
  名称：

  N-tert-Butanesulfinyl imine and aromatic tertiary amide derived non-biaryl atropisomers as chiral ligands for silver-catalyzed endo-selective [3+2] cycloaddition of azomethine ylides with maleimides

  摘要：

  Simple modifications of our novel ligand (Xing-Phos) were presented in this work, and a series of aromatic tertiary amide derived non-biaryl atropisomers were successfully synthesized in good yields. In addition, it was found that the multifunctional aromatic tertiary amide derived non-biaryl atropisomers exhibited an excellent endo-selectivity in the silver-catalyzed [3+2]-cycloaddition of azomethine ylides with N-aromatic maleimide. And especially, good to high levels of enantioselectivity (up to 98% ee) was obtained with a wide range of substrates in the presence of syn-(R, R-S)-2a (Xing-Phos). Furthermore, on the basis of the experimental data, it was demonstrated that a trace amount of water play an important role in the enhancement of enantioselectivity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.068

文献信息

• A novel Fe(II)/diaryl prolinol catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with alkenes
  作者：Haisheng Wu、Bo Wang、Hongqiang Liu、Lei Wang

  DOI：10.1016/j.tet.2010.11.091

  日期：2011.2

  A novel Fe(II)/diaryl prolinol catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with alkenes has been developed. In the presence of FeCl2 (10 mol %) and α,α-bis(3,5-bistrifluoromethylphenyl)prolinol L1 (10 mol %), [3+2] cycloaddition of azomethine ylides with electronic-deficient olefins underwent smoothly in CH3CN at room temperature to generate the desired endo-adducts in moderate

  已开发出一种新型的Fe（II）/二芳基脯氨醇催化的亚甲亚胺烷基化物与烯烃的不对称1,3-偶极环加成反应。在FeCl 2（10摩尔％）和α，α-双（3,5-双三氟甲基苯基）脯氨醇L1（10摩尔％）的存在下，[3 + 2]偶氮甲亚胺与电子不足的烯烃的环加成反应在CH中顺利进行3 CN在室温下以中等至良好的收率和对映选择性生成所需的内加合物。这是Fe（II）/ N，O-配体（L1）催化的甲亚胺基亚胺的1,3-偶极对映选择性环加成反应的第一个例子。
• Axially Chiral BINIM and Ni(II)-Catalyzed Highly Enantioselective 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides and <i>N</i>-Arylmaleimides
  作者：Jing-Wen Shi、Mei-Xin Zhao、Zhi-Yu Lei、Min Shi

  DOI：10.1021/jo701561d

  日期：2008.1.1

  [GRAPHICS]Axially chiral BINIM-Ni(II) complexes are effective catalysts in the asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides and N-arylmaleimides to give the corresponding adducts in good yields and up to 95% enantiomeric excesses.