[3S,5R]-(-)-3-methyl-5-phenyl-1-(p-toluenesulfonyl)pyrrolidin-2-one

• 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: [3S,5R]-(-)-3-methyl-5-phenyl-1-(p-toluenesulfonyl)pyrrolidin-2-one
• 英文别名: (3S,5R)-3-methyl-1-(4-methylphenyl)sulfonyl-5-phenylpyrrolidin-2-one
• 化学式: C₁₈H₁₉NO₃S
• 分子量: 329.42
• InChiKey: AEDDNWNQLLRSAL-WMLDXEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [2S,4R]-(+)-methyl 2-methyl-4-phenyl-4-(p-toluenesulfonylamino)butanoate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以74%的产率得到[3S,5R]-(-)-3-methyl-5-phenyl-1-(p-toluenesulfonyl)pyrrolidin-2-one
  参考文献：
  名称：

  Aziridine Ring-Opening Reactions with Chiral Enolates. Stereocontrolled Synthesis of 5-Substituted-3-methyl-pyrrolidin-2-ones

  摘要：

  A procedure for performing stereocontrolled aziridine ring-opening reactions with chiral enolates derived from (S,S)-(+)-pseudoephedrine amides has been developed leading to gamma -aminoamides in good yields. The diastereoselectivity of the reaction becomes controlled by the presence of the chiral auxiliary on the enolate, although the stereogenic center contained in the structure of the aziridine has a striking influence on the stereochemical course of the reaction which results in the presence of the corresponding matched and mismatched combinations. Besides, the sense of the asymmetric induction of the chiral auxiliary has resulted to be the opposite to the one found with other type of electrophiles, although it is in good agreement with the trend observed in the reaction of the same kind of enolates with epoxides. Finally, the obtained gamma -aminoamide adducts were converted into enantiopure gamma -amino acids, gamma -aminoesters, and pyrrolidin-2-ones using easy to perform and high yielding reactions.

  DOI：

  10.1021/jo0103571

文献信息

• Aziridine Ring-Opening Reactions with Chiral Enolates. Stereocontrolled Synthesis of 5-Substituted-3-methyl-pyrrolidin-2-ones
  作者：Jose L. Vicario、Dolores Badía、Luisa Carrillo

  DOI：10.1021/jo0103571

  日期：2001.8.1

  A procedure for performing stereocontrolled aziridine ring-opening reactions with chiral enolates derived from (S,S)-(+)-pseudoephedrine amides has been developed leading to gamma -aminoamides in good yields. The diastereoselectivity of the reaction becomes controlled by the presence of the chiral auxiliary on the enolate, although the stereogenic center contained in the structure of the aziridine has a striking influence on the stereochemical course of the reaction which results in the presence of the corresponding matched and mismatched combinations. Besides, the sense of the asymmetric induction of the chiral auxiliary has resulted to be the opposite to the one found with other type of electrophiles, although it is in good agreement with the trend observed in the reaction of the same kind of enolates with epoxides. Finally, the obtained gamma -aminoamide adducts were converted into enantiopure gamma -amino acids, gamma -aminoesters, and pyrrolidin-2-ones using easy to perform and high yielding reactions.