(2R,3S)-1-(t-butoxycarbonyl)-3-(3-methoxyphenyl)-N-phenylaziridine-2-carboxamide | 1073903-16-8

• 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)-3-(3-methoxyphenyl)-N-phenylaziridine-2-carboxamide
• 英文别名: tert-butyl (2S,3R)-2-(3-methoxyphenyl)-3-(phenylcarbamoyl)aziridine-1-carboxylate
• CAS: 1073903-16-8
• 化学式: C₂₁H₂₄N₂O₄
• 分子量: 368.433
• InChiKey: XUSRPWWNSJDHQF-BSKKSYLPSA-N

物化性质

• 沸点：
  556.7±50.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tert-butyl 3-methoxybenzylidenecarbamate 、 2-diazo-N-phenylacetamide 在 (S)-1,1-bis(2-biphenyl)-2-phenylethanediol 、 2-羧基苯硼酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以68%的产率得到(2R,3S)-1-(t-butoxycarbonyl)-3-(3-methoxyphenyl)-N-phenylaziridine-2-carboxamide
  参考文献：
  名称：

  In Situ Assembled Boronate Ester Assisted Chiral Carboxylic Acid Catalyzed Asymmetric Trans-Aziridinations

  摘要：

  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.

  DOI：

  10.1021/ja407764u

文献信息

• 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.
• 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.