(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-phenyl-3-(4-(trifluoromethyl)phenyl)propan-1-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S,3R)-3-(tert-butyldimethylsilyloxy)-2-phenyl-3-(4-(trifluoromethyl)phenyl)propan-1-ol
• 英文别名: (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-phenyl-3-[4-(trifluoromethyl)phenyl]propan-1-ol
• 化学式: C₂₂H₂₉F₃O₂Si
• 分子量: 410.552
• InChiKey: VXZWBPDIQIXLSF-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(三氟甲基)苄醇 在 咪唑 、 辛酸铑 作用下， 以 二氯甲烷 为溶剂， 反应 19.75h， 生成 (2S,3R)-3-(tert-butyldimethylsilyloxy)-2-phenyl-3-(4-(trifluoromethyl)phenyl)propan-1-ol
  参考文献：
  名称：

  Asymmetric Intermolecular C−H Functionalization of Benzyl Silyl Ethers Mediated by Chiral Auxiliary-Based Aryldiazoacetates and Chiral Dirhodium Catalysts

  摘要：

  C-H functionalization of benzyl silyl ethers by means of rhodium-catalyzed insertions of aryldiazoacetates can be achieved in a highly diastereoselective and enantioselective manner by judicious choice of chiral catalyst or auxiliary. The dirhodium tetraprolinates such as Rh-2((S)-DOSP)(4) have been widely successful as chiral catalysts in the C-H functionalization chemistry of aryldiazoacetates, but give poor enantioselectivity in the reactions of aryldiazoacetates with benzyl silyl ether derivatives. The use of (S)-lactate as a chiral auxiliary resulted in C-H functionalization with moderately high diastereoselectivity (79-88% de) and enantioselectivity (68-85% ee). The best results (91-95% de, 95-98% ee), however, were achieved using Hashimoto's Rh-2((S)-PTTL)(4) catalyst.

  DOI：

  10.1021/jo051747g

文献信息

• Asymmetric Intermolecular C−H Functionalization of Benzyl Silyl Ethers Mediated by Chiral Auxiliary-Based Aryldiazoacetates and Chiral Dirhodium Catalysts
  作者：Huw M. L. Davies、Simon J. Hedley、Brooks R. Bohall

  DOI：10.1021/jo051747g

  日期：2005.12.1

  C-H functionalization of benzyl silyl ethers by means of rhodium-catalyzed insertions of aryldiazoacetates can be achieved in a highly diastereoselective and enantioselective manner by judicious choice of chiral catalyst or auxiliary. The dirhodium tetraprolinates such as Rh-2((S)-DOSP)(4) have been widely successful as chiral catalysts in the C-H functionalization chemistry of aryldiazoacetates, but give poor enantioselectivity in the reactions of aryldiazoacetates with benzyl silyl ether derivatives. The use of (S)-lactate as a chiral auxiliary resulted in C-H functionalization with moderately high diastereoselectivity (79-88% de) and enantioselectivity (68-85% ee). The best results (91-95% de, 95-98% ee), however, were achieved using Hashimoto's Rh-2((S)-PTTL)(4) catalyst.