(1R,2S)-2-(4-methylphenyl)-cyclopent-3-enyl ethyl carbonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S)-2-(4-methylphenyl)-cyclopent-3-enyl ethyl carbonate
• 英文别名: ethyl [(1R,2S)-2-(4-methylphenyl)cyclopent-3-en-1-yl] carbonate
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: ATPHNWKJTYRYGK-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲苯硼酸 、 cyclopent-4-ene-1,3-diyl diethyl dicarbonate 在 [Rh(OH)(cod)]2 、 (S)-Xyl-P-PHOS caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 、 (1S,2R)-2-(4-methylphenyl)-cyclopent-3-enyl ethyl carbonate 、 (1R,2S)-2-(4-methylphenyl)-cyclopent-3-enyl ethyl carbonate
  参考文献：
  名称：

  Rhodium-Catalyzed Asymmetric Allylic Substitution with Boronic Acid Nucleophiles

  摘要：

  An enantio-, regio-, and diastereoselective rhodium(I)-catalyzed desymmetrization of a meso-cyclic allylic dicarbonate with organoboronic acid nucleophiles is described. The rhodium(I) catalyst formed in situ from [Rh(cod)OH](2) and Xyl-P-PHOS allowed the S(N)2' allylic substitution product to be obtained with a range of arylboronic acids in enantiomeric excesses of up to 92% with regioselectivities of up to > 20:1.

  DOI：

  10.1021/ol061777l

文献信息

• Rhodium-Catalyzed Asymmetric Allylic Substitution with Boronic Acid Nucleophiles
  作者：Frederic Menard、Timothy M. Chapman、Chris Dockendorff、Mark Lautens

  DOI：10.1021/ol061777l

  日期：2006.9.1

  An enantio-, regio-, and diastereoselective rhodium(I)-catalyzed desymmetrization of a meso-cyclic allylic dicarbonate with organoboronic acid nucleophiles is described. The rhodium(I) catalyst formed in situ from [Rh(cod)OH](2) and Xyl-P-PHOS allowed the S(N)2' allylic substitution product to be obtained with a range of arylboronic acids in enantiomeric excesses of up to 92% with regioselectivities of up to > 20:1.