(S)-1-benzyl-3-(3,5-dimethylphenyl)pyrrolidine-2,5-dione

• 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: (S)-1-benzyl-3-(3,5-dimethylphenyl)pyrrolidine-2,5-dione
• 英文别名: (3S)-1-benzyl-3-(3,5-dimethylphenyl)pyrrolidine-2,5-dione
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: YCHDEZIAPUWOAO-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-苄基马来酰亚胺 、 3,5-二甲基苯硼酸 在 C₄₂H₄₆O₆Rh₂S₂ 、 cesium fluoride 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以85%的产率得到(S)-1-benzyl-3-(3,5-dimethylphenyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Sulfoxide–Alkene Hybrids: A New Class of Chiral Ligands for the Hayashi–Miyaura Reaction

  摘要：

  Sulfoxide-alkene hybrids are introduced as a new class of chiral heterodentate ligands for the Hayashi-Miyaura reaction. The synthesis of these ligands was achieved without the use of protecting groups. A chiral resolution was performed via simple column-chromatographic separation of the diastereomeric ligands. Both diastereomers proved to be excellent ligands In Rh-catalyzed 1,4-addition reactions, furnishing chiral Products with high enantloselectivities and, remarkably, opposite stereoconfigurations.

  DOI：

  10.1021/ol200841x

文献信息

• Room-Temperature Rh-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Maleimides and Enones in the Presence of CF₃-Substituted MeOBIPHEP Analogues
  作者：Florent Le Boucher d’Herouville、Anthony Millet、Michelangelo Scalone、Véronique Michelet

  DOI：10.1021/jo201073y

  日期：2011.8.19

  has been developed for the 1,4-addition of boronic acids to maleimides and enones under mild conditions at room temperature and led to succinimide derivatives and arylated cyclic ketones in good to excellent yields and ee. We uncovered the crucial role of the electronic and steric properties of diphosphine ligand and observed a strong boronic acid/ligand dependency in the case of maleimide derivatives

  已开发出一种含Rh的催化体系，该体系暗示贫电子的MeOBIPHEP类似物，可在室温下于室温下将1，4-硼酸加成到马来酰亚胺和烯酮中，并导致琥珀酰亚胺衍生物和芳基化的环状酮，具有优异的收率和优异的收率。 ee。我们发现了二膦配体的电子和空间特性的关键作用，并且在马来酰亚胺衍生物的情况下观察到强烈的硼酸/配体依赖性，在环烯酮的情况下观察到底物/配体匹配。
• Chiral Phosphine-Olefin Bidentate Ligands in Asymmetric Catalysis: Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl Boronic Acids to Maleimides
  作者：Ryo Shintani、Wei-Liang Duan、Takashi Nagano、Atsushi Okada、Tamio Hayashi

  DOI：10.1002/anie.200501305

  日期：2005.7.18