(R)-1-benzyl-5-chloro-3-hydroxy-3-phenylindolin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-1-benzyl-5-chloro-3-hydroxy-3-phenylindolin-2-one
• 英文别名: (3R)-1-benzyl-5-chloro-3-hydroxy-3-phenylindol-2-one
• 化学式: C₂₁H₁₆ClNO₂
• 分子量: 349.817
• InChiKey: RYGMVWVQHKQUNF-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯靛红 在 chlorobis(ethylene)rhodium(I) dimer 、 (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphine 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.0h， 生成 (R)-1-benzyl-5-chloro-3-hydroxy-3-phenylindolin-2-one
  参考文献：
  名称：

  Rh（I）催化将芳基硼酸不对称加成到NH靛红中

  摘要：

  标题反应的过渡金属催化的不对称变体通常限于N-保护的靛红。然而，发现在温和条件下，Rh（I）/手性亚砜膦配合物可催化将芳基硼酸对映选择性加成至NH靛红。以高收率和良好至优异的对映选择性（85-92％ee）获得了各种手性3-芳基-3-羟基-3-羟吲哚。

  DOI：

  10.1016/j.tetasy.2012.04.013

文献信息

• A C=O⋅⋅⋅Isothiouronium Interaction Dictates Enantiodiscrimination in Acylative Kinetic Resolutions of Tertiary Heterocyclic Alcohols
  作者：Mark D. Greenhalgh、Samuel M. Smith、Daniel M. Walden、James E. Taylor、Zamira Brice、Emily R. T. Robinson、Charlene Fallan、David B. Cordes、Alexandra M. Z. Slawin、H. Camille Richardson、Markas A. Grove、Paul Ha‐Yeon Cheong、Andrew D. Smith

  DOI：10.1002/anie.201712456

  日期：2018.3.12

  C=O⋅⋅⋅isothiouronium interaction as key to efficient enantiodiscrimination in the kinetic resolution of tertiary heterocyclic alcohols bearing up to three potential recognition motifs at the stereogenic tertiary carbinol center. This discrimination was exploited in the isothiourea‐catalyzed acylative kinetic resolution of tertiary heterocyclic alcohols (38 examples, s factors up to >200). The reaction proceeds at low

  实验和计算研究的结合已经确定 C=O⋅⋅⋅isothiouronium 相互作用是在立体叔甲醇中心承载多达三个潜在识别基序的叔杂环醇的动力学分辨率中有效对映体区分的关键。这种区分在异硫脲催化的叔杂环醇的酰基化动力学拆分中得到了利用（38 个例子，s 因子高达 >200）。该反应在低催化剂负载量（通常为 1 mol%）下进行，异丁酸或乙酸酐作为酰化剂在温和条件下进行。
• Me-BIPAM for the Synthesis of Optically Active 3-Aryl-3-hydroxy-2-oxindoles by Ruthenium-catalyzed Addition of Arylboronic Acids to Isatins
  作者：Yasunori Yamamoto、Masaaki Yohda、Tomohiko Shirai、Hajime Ito、Norio Miyaura

  DOI：10.1002/asia.201200481

  日期：2012.10

  arylboronic acids to isatins. Asymmetric synthesis of 3‐aryl‐3‐hydroxy‐2‐oxindoles by 1,2‐addition of arylboronic acids to isatins was carried out in the presence of [RuCl2(PPh3)3]/(R,R)‐Me‐BIPAM and KF, resulting in an enantioselectivity as high as 90 % ee. It was found that the reaction with N‐protected isatins proceeds with high yields and good enantioselectivities. The best protective groups on the

  一个手性的O-连接的C 2-对称的二齿亚磷酰胺（Me-BIPAM）被发现对于钌催化的芳基硼酸到靛红的加成反应是有效的。在[RuCl 2（PPh 3）3 ] /（R，R）-Me-的存在下，通过将芳基硼酸1,2-加成到靛红中进行3-芳基-3-羟基-2-氧吲哚的不对称合成。BIPAM和KF，对映选择性高达90％ee。发现与N保护的靛红的反应以高收率和良好的对映选择性进行。氮原子上的最佳保护基根据芳环上的取代基而不同。使用一个与其他基团相比，N-苄基在许多底物中均具有出色的对映选择性。
• Synthesis of a Class of Chiral-Bridged Phosphoramidite Ligands and Their Applications in the First Iridium-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatins
  作者：Yue Zhuang、Yuwei He、Zihong Zhou、Wang Xia、Chuyu Cheng、Meng Wang、Bin Chen、Zhongyuan Zhou、Jiyan Pang、Liqin Qiu

  DOI：10.1021/acs.joc.5b00595

  日期：2015.7.17

  A series of novel chiral phosphoramidite ligands based on chiral-bridged biphenyl backbones have been prepared conveniently and characterized. The ligands complexed with [IrCodCl](2) provided the first iridium catalyst system for the asymmetric addition of arylboronic acids to N-protected isatins with high efficiency. When performed in THF/H2O at 80 degrees C with 2 equiv of the arylboronic acids, the transformations acquired good to excellent results (up to 98% yield and 95% ee).
• Rh(I)-catalyzed asymmetric 1,2-additions of arylboronic acids to isatins with chiral sulfur–alkene hybrid ligands
  作者：Xiangqing Feng、Yanzhao Nie、Lanqiong Zhang、Jing Yang、Haifeng Du

  DOI：10.1016/j.tetlet.2014.06.074

  日期：2014.8

  A rhodium-catalyzed asymmetric 1,2-addition of arylboronic acids to isatins with chiral sulfur-alkene hybrid ligands was achieved, and a variety of 3-aryl-3-hydroxy-2-oxindoles were obtained in moderate to good yields with up to 85% ee and a biologically active compound was synthesized with this strategy. (C) 2014 Elsevier Ltd. All rights reserved.
• Rhodium-Catalyzed Asymmetric Addition of Aryl- and Alkenylboronic Acids to Isatins
  作者：Ryo Shintani、Mitsunori Inoue、Tamio Hayashi

  DOI：10.1002/anie.200600392

  日期：2006.5.12