(3S)-2-methylsulfonyl-3-phenyloxaziridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哑嗪
• 英文名称: (3S)-2-methylsulfonyl-3-phenyloxaziridine
• 化学式: C₈H₉NO₃S
• 分子量: 199.23
• InChiKey: MQLZOPXMXAGMJH-IENPIDJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-methanesulfonyl benzylideneamine 在 1-(2,2-dimethylpropyl)-3-[(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]thiourea 、 间氯过氧苯甲酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以35%的产率得到
  参考文献：
  名称：

  Novel chiral thiourea organocatalysts for the catalytic asymmetric oxaziridination

  摘要：

  Catalytic enantioselective oxaziridination is one of the challenging reactions in the oxidation of organic molecules. In this article, a series of novel chiral thiourea moleculars were synthesized from natural cinchona alkaloids and primary amines. By using these molecules as organocatalysts and m-chloroper-oxybenzoicacid (m-CPBA) as the oxidant, a methodology on highly enantioselective epoxidation of al-dimines has been developed. Several optically active oxaziridines have been constructed in good yields (up to 95%) and moderate to excellent enantioselectivities (up to 99% ee). A plausible transition state was also proposed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.12.010

文献信息

• Novel chiral thiourea organocatalysts for the catalytic asymmetric oxaziridination
  作者：Nan Ji、Jiani Yuan、Shanshan Xue、Junna Zhang、Wei He

  DOI：10.1016/j.tet.2015.12.010

  日期：2016.1

  Catalytic enantioselective oxaziridination is one of the challenging reactions in the oxidation of organic molecules. In this article, a series of novel chiral thiourea moleculars were synthesized from natural cinchona alkaloids and primary amines. By using these molecules as organocatalysts and m-chloroper-oxybenzoicacid (m-CPBA) as the oxidant, a methodology on highly enantioselective epoxidation of al-dimines has been developed. Several optically active oxaziridines have been constructed in good yields (up to 95%) and moderate to excellent enantioselectivities (up to 99% ee). A plausible transition state was also proposed. (C) 2015 Elsevier Ltd. All rights reserved.