(2R,3S)-1-(t-butoxycarbonyl)-N-(4-chlorophenyl)-3-phenylaziridine-2-carboxamide | 1073903-27-1

• 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: (2R,3S)-1-(t-butoxycarbonyl)-N-(4-chlorophenyl)-3-phenylaziridine-2-carboxamide
• CAS: 1073903-27-1
• 化学式: C₂₀H₂₁ClN₂O₃
• 分子量: 372.851
• InChiKey: PJOBAHXHIPDMQR-MSNHYEFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.41
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  N-p-chlorophenyl-α-diazoacetamide 、 benzaldehyde N-boc imine 在 (R)-3,3'-dimesityl-1,1'-binaphthyl-2,2'-dicarboxylic acid 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以60%的产率得到(2R,3S)-1-(t-butoxycarbonyl)-N-(4-chlorophenyl)-3-phenylaziridine-2-carboxamide
  参考文献：
  名称：

  Trans-Selective Asymmetric Aziridination of Diazoacetamides and N-Boc Imines Catalyzed by Axially Chiral Dicarboxylic Acid

  摘要：

  Axially chiral dicarboxylic acid (R)-1d catalyzed reaction of diazoacetamides and N-Boc imines provided a novel organocatalytic means for the formation of enantiomerically enriched N-Boc protected trans aziridines.

  DOI：

  10.1021/ja805635c

文献信息

• Highly Efficient Asymmetric <i>Trans-</i>Selective Aziridination of Diazoacetamides and <i>N</i>-Boc-imines Catalyzed by Chiral Brønsted Acids
  作者：Xiaofei Zeng、Xin Zeng、Zhenjiang Xu、Min Lu、Guofu Zhong

  DOI：10.1021/ol901047w

  日期：2009.7.16

  A clean and fast (10 min) aziridination of diazoacetamides with N-Boc-imines, as well as N-Cbz-imines, catalyzed by chiral phosphoric acid (R)-5g in DCM at room temperature was developed, The excellent yields (89-97%), diastereoselectivities (trans/cis > 50:1), chemoselectivities (3:4 = >95:5), and enantioselectivities (88-98% ee) were achieved in the reaction.