(4S)-N-tert-butoxycarbonyl-4-[(diphenylphosphinoyl)methyl]-2,2-dimethyl-1,3-oxazolidine | 943599-10-8

• 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: (4S)-N-tert-butoxycarbonyl-4-[(diphenylphosphinoyl)methyl]-2,2-dimethyl-1,3-oxazolidine
• 英文别名: tert-butyl (4S)-4-(diphenylphosphorylmethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 943599-10-8
• 化学式: C₂₃H₃₀NO₄P
• 分子量: 415.469
• InChiKey: RINPHLQWGUSVHQ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-N-tert-butoxycarbonyl-4-[(diphenylphosphinoyl)methyl]-2,2-dimethyl-1,3-oxazolidine 在 盐酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 氯苯 为溶剂， 反应 30.0h， 生成 2,2-bis[(4S)-4-(diphenylphosphinoyl)methyl-1,3-oxazolin-2-yl]propane
  参考文献：
  名称：

  Enantioselective allylation of aldehydes catalyzed by new bifunctional bisoxazoline–metal complexes

  摘要：

  The asymmetric allylation reactions of aldehydes catalyzed by a 10 mol % bisoxazoline complex bearing a phosphine oxide moiety, which was newly designed and synthesized from L-serine, afforded the corresponding homoallylic alcohols in 48-74% yields with 39-86% ee. The reaction proceeds with the dual activation of the aldehyde and allylsilane by the Lewis acid and base of the catalyst. The evidence for the activation of the allylsilane was clarified by the P-31 NMR spectra. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.104
• 作为产物：
  描述：

  (S)-N-Boc-2,2-dimethyl-4-(tosyloxymethyl)oxazolidine 在 potassium tert-butylate 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (4S)-N-tert-butoxycarbonyl-4-[(diphenylphosphinoyl)methyl]-2,2-dimethyl-1,3-oxazolidine
  参考文献：
  名称：

  Enantioselective allylation of aldehydes catalyzed by new bifunctional bisoxazoline–metal complexes

  摘要：

  The asymmetric allylation reactions of aldehydes catalyzed by a 10 mol % bisoxazoline complex bearing a phosphine oxide moiety, which was newly designed and synthesized from L-serine, afforded the corresponding homoallylic alcohols in 48-74% yields with 39-86% ee. The reaction proceeds with the dual activation of the aldehyde and allylsilane by the Lewis acid and base of the catalyst. The evidence for the activation of the allylsilane was clarified by the P-31 NMR spectra. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.104

文献信息

• Enantioselective allylation of aldehydes catalyzed by new bifunctional bisoxazoline–metal complexes
  作者：Keiichi Takeuchi、Takuma Takeda、Tetsuya Fujimoto、Iwao Yamamoto

  DOI：10.1016/j.tet.2007.02.104

  日期：2007.6

  The asymmetric allylation reactions of aldehydes catalyzed by a 10 mol % bisoxazoline complex bearing a phosphine oxide moiety, which was newly designed and synthesized from L-serine, afforded the corresponding homoallylic alcohols in 48-74% yields with 39-86% ee. The reaction proceeds with the dual activation of the aldehyde and allylsilane by the Lewis acid and base of the catalyst. The evidence for the activation of the allylsilane was clarified by the P-31 NMR spectra. (c) 2007 Elsevier Ltd. All rights reserved.