(+)-(3R,5S)-2-N-benzyl-5-ethoxy-isoxazolidine-3-carboxylic acid ethyl ester | 223588-06-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-(3R,5S)-2-N-benzyl-5-ethoxy-isoxazolidine-3-carboxylic acid ethyl ester
• 英文别名: ethyl (3R,5S)-2-benzyl-5-ethoxy-1,2-oxazolidine-3-carboxylate
• CAS: 223588-06-5
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: UOUKQMHYOZQHOO-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-(3R,5S)-2-N-benzyl-5-ethoxy-isoxazolidine-3-carboxylic acid ethyl ester 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (+)-(3R,5S)-2-N-benzyl-5-ethoxy-isoxazolidine-3-carboxylic acid
  参考文献：
  名称：

  Copper(II)-Bisoxazoline Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions of Nitrones with Electron-Rich Alkenes

  摘要：

  A transition-metal-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition reaction between electrophilic nitrones and electron-rich alkenes has been developed employing chiral copper(II)- and zinc(II)-bisoxazolines as catalysts. In the presence of Cu(OTf)(2)-bisoxazoline as the catalyst, the nitrones, which coordinate to the chiral catalyst in a bidentate fashion, reacted smoothly with alkenes at room temperature to give isoxazolidines in good yields and diastereoselectivity and with high enantioselectivities of up to 94% ee. The influence of the metal salts, chiral ligands, and solvents on the reaction course has been investigated, and a general reaction protocol is developed. On the basis of the absolute stereochemistry of the 1,3-dipolar cycloaddition product, the coordination of the nitrone to the catalyst is discussed and a mechanistic approach of the reaction is presented. It is proposed that the intermediate is one in which both the nitrone and alkene are coordinated to the chiral copper(II)-bisoxazoline catalyst.

  DOI：

  10.1021/jo982081b
• 作为产物：
  描述：

  N-benzyl-α-ethoxycarbonylmethanimine N-oxide 、 乙烯基乙醚 以 甲苯 为溶剂， 反应 23.0h， 生成 (3S,5S)-2-Benzyl-5-ethoxy-isoxazolidine-3-carboxylic acid ethyl ester 、 (+)-(3R,5S)-2-N-benzyl-5-ethoxy-isoxazolidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Copper(II)-Bisoxazoline Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions of Nitrones with Electron-Rich Alkenes

  摘要：

  A transition-metal-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition reaction between electrophilic nitrones and electron-rich alkenes has been developed employing chiral copper(II)- and zinc(II)-bisoxazolines as catalysts. In the presence of Cu(OTf)(2)-bisoxazoline as the catalyst, the nitrones, which coordinate to the chiral catalyst in a bidentate fashion, reacted smoothly with alkenes at room temperature to give isoxazolidines in good yields and diastereoselectivity and with high enantioselectivities of up to 94% ee. The influence of the metal salts, chiral ligands, and solvents on the reaction course has been investigated, and a general reaction protocol is developed. On the basis of the absolute stereochemistry of the 1,3-dipolar cycloaddition product, the coordination of the nitrone to the catalyst is discussed and a mechanistic approach of the reaction is presented. It is proposed that the intermediate is one in which both the nitrone and alkene are coordinated to the chiral copper(II)-bisoxazoline catalyst.

  DOI：

  10.1021/jo982081b

文献信息

• Copper(II)-Bisoxazoline Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions of Nitrones with Electron-Rich Alkenes
  作者：Kim B. Jensen、Rita G. Hazell、Karl Anker Jørgensen

  DOI：10.1021/jo982081b

  日期：1999.4.1

  A transition-metal-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition reaction between electrophilic nitrones and electron-rich alkenes has been developed employing chiral copper(II)- and zinc(II)-bisoxazolines as catalysts. In the presence of Cu(OTf)(2)-bisoxazoline as the catalyst, the nitrones, which coordinate to the chiral catalyst in a bidentate fashion, reacted smoothly with alkenes at room temperature to give isoxazolidines in good yields and diastereoselectivity and with high enantioselectivities of up to 94% ee. The influence of the metal salts, chiral ligands, and solvents on the reaction course has been investigated, and a general reaction protocol is developed. On the basis of the absolute stereochemistry of the 1,3-dipolar cycloaddition product, the coordination of the nitrone to the catalyst is discussed and a mechanistic approach of the reaction is presented. It is proposed that the intermediate is one in which both the nitrone and alkene are coordinated to the chiral copper(II)-bisoxazoline catalyst.