(2R)-2-[1-(tert-butoxycarbonyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-hydroxyacetic acid n-butyl ester | 1338919-53-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (2R)-2-[1-(tert-butoxycarbonyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-hydroxyacetic acid n-butyl ester
• 英文别名: tert-butyl 3-[(1R)-2-butoxy-1-hydroxy-2-oxoethyl]-2,5-dimethylpyrrole-1-carboxylate
• CAS: 1338919-53-1
• 化学式: C₁₇H₂₇NO₅
• 分子量: 325.405
• InChiKey: OEWCOFVDKAMRDD-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 2,5-dimethyl-1H-pyrrole-1-carboxylate 、 乙醛酸正丁酯 在 titanium(IV) isopropylate 、 (R)-6,6'-dibromo-1,1'-binaphth-2-ol 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以91%的产率得到(2R)-2-[1-(tert-butoxycarbonyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-hydroxyacetic acid n-butyl ester
  参考文献：
  名称：

  Enantioselective Friedel–Crafts Reaction of Acylpyrroles with Glyoxylates Catalyzed by BINOL–Ti(IV) Complexes

  摘要：

  We report the first efficient enantioselective Friedel-Crafts hydroxyalkylation of pyrroles having one electron-withdrawing group at the alpha, beta or N-positions with alkyl glyoxylates catalyzed by readily available chiral BINOL-Ti(IV) complexes (1-5 mol %). The reaction regioselectively led to the desired pyrrole-hydroxyacetic acid derivatives with good yields (70-96%) and enantiomeric excesses up to 96%, and is applicable in multigram scale with low loading of the catalyst (1 mol %).

  DOI：

  10.1021/ol202244u

文献信息

• Enantioselective Friedel–Crafts Reaction of Acylpyrroles with Glyoxylates Catalyzed by BINOL–Ti(IV) Complexes
  作者：Jakub Majer、Piotr Kwiatkowski、Janusz Jurczak

  DOI：10.1021/ol202244u

  日期：2011.11.18

  We report the first efficient enantioselective Friedel-Crafts hydroxyalkylation of pyrroles having one electron-withdrawing group at the alpha, beta or N-positions with alkyl glyoxylates catalyzed by readily available chiral BINOL-Ti(IV) complexes (1-5 mol %). The reaction regioselectively led to the desired pyrrole-hydroxyacetic acid derivatives with good yields (70-96%) and enantiomeric excesses up to 96%, and is applicable in multigram scale with low loading of the catalyst (1 mol %).