(S)-tert-butyl 2-(2-iodobenzyl)indoline-2-carboxylate | 1394351-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (S)-tert-butyl 2-(2-iodobenzyl)indoline-2-carboxylate
• 英文别名: tert-butyl 2-(2-iodobenzyl)indoline-2-carboxylate
• CAS: 1394351-07-5
• 化学式: C₂₀H₂₂INO₂
• 分子量: 435.305
• InChiKey: VYOPQCOPPULCLF-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-碘苯甲基溴 在 盐酸 、 copper(l) iodide 、 硫酸 、 (R)-3,3′-二-9-蒽基-1,1′-二-2-萘酚 、 水 、 四丁基硫酸氢铵 、 potassium carbonate 、 caesium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 乙腈 为溶剂， 反应 39.0h， 生成 (S)-tert-butyl 2-(2-iodobenzyl)indoline-2-carboxylate
  参考文献：
  名称：

  Copper-Catalyzed Desymmetric Intramolecular Ullmann C–N Coupling: An Enantioselective Preparation of Indolines

  摘要：

  The first highly enantioselective copper-catalyzed intramolecular Ullmann C-N coupling reaction has been developed. The asymmetric desymmetrization of 1,3-bis(2-iodoaryl)propan-2-amines catalyzed by CuI/(R)-BINOL-derived ligands led to the enantioselective formation of indolines in high yields and excellent enantiomeric excesses. This method was also applied to the formation of 1,2,3,4-tetrahydroquinolines in high yields and excellent enantioselectivity.

  DOI：

  10.1021/ja306631z

文献信息

• Development and Challenges in Copper-Catalyzed Asymmetric Ullmann-Type Coupling Reactions
  作者：Qian Cai、Fengtao Zhou

  DOI：10.1055/s-0032-1317866

  日期：——

  Ullmann-type coupling is one of the most powerful methods for the formation of aryl C–C, C–N, and C–O bonds. Yet asymmetric Ullmann coupling has received little attention because of the great challenges in both ligand and reaction designs. The success of the first catalytic enantioselective intramolecular Ullmann C–N coupling reaction through an asymmetric desymmetrization strategy offers a new way

  Ullmann 型偶联是形成芳基 C-C、C-N 和 C-O 键的最有效方法之一。然而，由于配体和反应设计中的巨大挑战，不对称 Ullmann 偶联很少受到关注。通过不对称去对称化策略的第一个催化对映选择性分子内 Ullmann C-N 偶联反应的成功为开发此类反应的对映选择性变体提供了一种新方法。本文阐述了去对称化策略在 Ullmann 型耦合中的重要性，并概述了该领域的一些未来方向。
• An Unexpected Inversion of Enantioselectivity in a Copper-Catalyzed Intramolecular­ Desymmetric Aryl C–N Coupling Reaction
  作者：Jiangguang Liu、Jiajie Yan、Dongguang Qin、Qian Cai

  DOI：10.1055/s-0033-1338638

  日期：——

  Enantioselective formation of indolines was achieved through desymmetrization of alpha,alpha-bis(2-iodobenzyl)glycines under the catalysis of copper(I) iodide and (2S, 3aS, 7aS)-octahydro-1H-indole-2-carboxylic acid. An unexpected inversion of enantioselectivity was observed when achiral additives such as 4-(N,N-dimethylamino)pyridine were added which work together with the ligand. The configuration-reversed products were obtained in moderate yields as well as moderate ee values.