(2R,3S)-1-benzyl-N-phenyl-3-(3-tolyl)aziridine-2-carboxamide

• 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-benzyl-N-phenyl-3-(3-tolyl)aziridine-2-carboxamide
• 英文别名: (2R,3S)-1-benzyl-3-(2-methylphenyl)-N-phenylaziridine-2-carboxamide
• 化学式: C₂₃H₂₂N₂O
• 分子量: 342.44
• InChiKey: AMCMRBLZLVVOKA-FQTTXOOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2-methylbenzylidene)-1-phenylmethanamine 、 2-diazo-N-phenylacetamide 在 2-borono-4-(trifluoromethyl)benzoic acid 、 (S)-1,1-bis(2-biphenyl)-2-phenylethanediol 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以74%的产率得到(2R,3S)-1-benzyl-N-phenyl-3-(3-tolyl)aziridine-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

• 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.