(3S,5S)-trans-N-benzoyl-5-(2-naphthyl)-3-phenylisoxazolidine | 1106719-24-7

• 英文名称: (3S,5S)-trans-N-benzoyl-5-(2-naphthyl)-3-phenylisoxazolidine
• CAS: 1106719-24-7
• 化学式: C₂₆H₂₁NO₂
• 分子量: 379.458
• InChiKey: YDXQOLNBNFHKCL-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  苯甲酰氯 、 5-(naphthalen-2-yl)-3-phenyl-4,5-dihydroisoxazole 在 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 dimethyl sulfide borane 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 乙醇 为溶剂， 反应 34.0h， 生成 (R)-5-(2-naphthyl)-3-phenyl-2-isoxazoline 、 (S)-5-(2-naphthyl)-3-phenyl-2-isoxazoline 、 (3S,5S)-trans-N-benzoyl-5-(2-naphthyl)-3-phenylisoxazolidine 、 (3S,5R)-cis-N-benzoyl-5-(2-naphthyl)-3-phenylisoxazolidine 、 (3R,5S)-cis-N-benzoyl-5-(2-naphthyl)-3-phenylisoxazolidine
  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