(3S,5S)-trans-N-benzoyl-3,5-diphenylisoxazolidine | 1106719-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3S,5S)-trans-N-benzoyl-3,5-diphenylisoxazolidine
• 英文别名: [(3S,5S)-3,5-diphenyl-1,2-oxazolidin-2-yl]-phenylmethanone
• CAS: 1106719-07-6
• 化学式: C₂₂H₁₉NO₂
• 分子量: 329.398
• InChiKey: ZLKRLAYRFHUTAM-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,5S)-trans-N-benzoyl-3,5-diphenylisoxazolidine 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 乙醇 为溶剂， 反应 21.0h， 生成 rac-(1S,3S)-3-benzoylamino-1,3-diphenyl-1-propanol
  参考文献：
  名称：

  Asymmetric reduction of racemic 2-isoxazolines

  摘要：

  The kinetic resolution of racemic 2-isoxazolines was carried out by asymmetric reduction using borane with 1,2-amino alcohols as a chiral Source. Using excess BH3-THF in the presence of (-)-norephedrine, optically active 1,3-amino alcohol derivatives were obtained with good ee but in lower yield, while the optically active substrates 2-isoxazolines were recovered with modest ee. The asymmetric reduction using 2.0 equiv of BH3-SMe2 was investigated as an alternative strategy for the synthesis of optically active products. After reduction, treatment of the resulting Mixture with Et3N was successful in providing optically active isoxazolidine derivatives in good yields and with good ee. The choice of chiral source was also shown to have a significant effect. In particular, the use of (S)-alpha,alpha-diphenyl-2-pyrrolidinemethanol reversed the enantioselectivity of the recovered Substrates. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.005
• 作为产物：
  描述：

  、 苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3S,5S)-trans-N-benzoyl-3,5-diphenylisoxazolidine 、 (3S,5R)-cis-N-benzoyl-3,5-diphenylisoxazolidine
  参考文献：
  名称：

  Asymmetric reduction of racemic 2-isoxazolines

  摘要：

  The kinetic resolution of racemic 2-isoxazolines was carried out by asymmetric reduction using borane with 1,2-amino alcohols as a chiral Source. Using excess BH3-THF in the presence of (-)-norephedrine, optically active 1,3-amino alcohol derivatives were obtained with good ee but in lower yield, while the optically active substrates 2-isoxazolines were recovered with modest ee. The asymmetric reduction using 2.0 equiv of BH3-SMe2 was investigated as an alternative strategy for the synthesis of optically active products. After reduction, treatment of the resulting Mixture with Et3N was successful in providing optically active isoxazolidine derivatives in good yields and with good ee. The choice of chiral source was also shown to have a significant effect. In particular, the use of (S)-alpha,alpha-diphenyl-2-pyrrolidinemethanol reversed the enantioselectivity of the recovered Substrates. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.005

文献信息

• Asymmetric reduction of racemic 2-isoxazolines
  作者：Masashi Tokizane、Kaori Sato、Tetsuo Ohta、Yoshihiko Ito

  DOI：10.1016/j.tetasy.2008.11.005

  日期：2008.11

  The kinetic resolution of racemic 2-isoxazolines was carried out by asymmetric reduction using borane with 1,2-amino alcohols as a chiral Source. Using excess BH3-THF in the presence of (-)-norephedrine, optically active 1,3-amino alcohol derivatives were obtained with good ee but in lower yield, while the optically active substrates 2-isoxazolines were recovered with modest ee. The asymmetric reduction using 2.0 equiv of BH3-SMe2 was investigated as an alternative strategy for the synthesis of optically active products. After reduction, treatment of the resulting Mixture with Et3N was successful in providing optically active isoxazolidine derivatives in good yields and with good ee. The choice of chiral source was also shown to have a significant effect. In particular, the use of (S)-alpha,alpha-diphenyl-2-pyrrolidinemethanol reversed the enantioselectivity of the recovered Substrates. (C) 2008 Elsevier Ltd. All rights reserved.