(E)-tert-butyl 4-oxo-4-((S)-2-oxo-4-phenyloxazolidin-3-yl)but-2-enoate | 1197006-42-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-tert-butyl 4-oxo-4-((S)-2-oxo-4-phenyloxazolidin-3-yl)but-2-enoate
• 英文别名: tert-butyl (E)-4-oxo-4-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]but-2-enoate
• CAS: 1197006-42-0
• 化学式: C₁₇H₁₉NO₅
• 分子量: 317.342
• InChiKey: RMEAGCOQFQXBCE-WTNCMQEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-tert-butyl 4-oxo-4-((S)-2-oxo-4-phenyloxazolidin-3-yl)but-2-enoate 、 N-(4-nitrobenzyl)benzimidoyl chloride 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以73%的产率得到(2'S,2R,3S,4S)-[3,4-dihydro-2-(4-nitrophenyl)-4-(2-oxo-4-phenyoxazolidin)-5-phenyl-2H-pyrrol-3-yl]-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid

  摘要：

  Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity In the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.

  DOI：

  10.1021/ol9018584
• 作为产物：
  描述：

  (S)-4-苯基-2-恶唑烷酮 、 (E)-3-chlorocarbonyl-acrylic acid tert-butyl ester 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (E)-tert-butyl 4-oxo-4-((S)-2-oxo-4-phenyloxazolidin-3-yl)but-2-enoate
  参考文献：
  名称：

  Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid

  摘要：

  Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity In the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.

  DOI：

  10.1021/ol9018584

文献信息

• Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid
  作者：Mukund P. Sibi、Takahiro Soeta、Craig P. Jasperse

  DOI：10.1021/ol9018584

  日期：2009.12.3

  Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity In the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.