(2S,3R)-1-(t-butoxycarbonyl)-N,3-diphenylaziridine-2-carboxamide | 1172133-01-5

• 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: (2S,3R)-1-(t-butoxycarbonyl)-N,3-diphenylaziridine-2-carboxamide
• 英文别名: tert-butyl (2R,3S)-2-phenyl-3-(phenylcarbamoyl)aziridine-1-carboxylate
• CAS: 1172133-01-5
• 化学式: C₂₀H₂₂N₂O₃
• 分子量: 338.406
• InChiKey: ILWJQHQQXJYDLL-KDPSSXBDSA-N

物化性质

• 沸点：
  529.8±50.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-diazo-N-phenylacetamide 、 benzaldehyde N-boc imine 在 (S)-3,3'-双(9-蒽基)-1,1'-联萘-2,2'-二基磷酸氢酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以95%的产率得到(2S,3R)-1-(t-butoxycarbonyl)-N,3-diphenylaziridine-2-carboxamide
  参考文献：
  名称：

  Highly Efficient Asymmetric Trans-Selective Aziridination of Diazoacetamides and N-Boc-imines Catalyzed by Chiral Brønsted Acids

  摘要：

  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.

  DOI：

  10.1021/ol901047w

文献信息

• In Situ Assembled Boronate Ester Assisted Chiral Carboxylic Acid Catalyzed Asymmetric Trans-Aziridinations
  作者：Takuya Hashimoto、Alberto Osuna Gálvez、Keiji Maruoka

  DOI：10.1021/ja407764u

  日期：2013.11.27

  We developed herein a new chiral Bronsted acid catalyst which is composed of two independent organic molecules, a chiral diol, and 2-boronobenzoic acid. In situ formation of a boronate ester was utilized as a key process to generate an active catalyst. This boronate ester assisted chiral carboxylic acid catalyst was successfully applied to the trans-aziridination of N-Boc and N-benzyl imines with N-phenyldiazoacetamide. This is the first catalyst to achieve high enantioselectivities using N-benzyl imines.
• Trans-Selective Asymmetric Aziridination of Diazoacetamides and <i>N</i>-Boc Imines Catalyzed by Axially Chiral Dicarboxylic Acid
  作者：Takuya Hashimoto、Nanase Uchiyama、Keiji Maruoka

  DOI：10.1021/ja805635c

  日期：2008.11.5

  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.
• 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.