dimethyl (2R,3R,4R,5S)-3-[(4R,5R)-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl]-5-phenylpyrrolidine-2,4-dicarboxylate | 135212-34-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: dimethyl (2R,3R,4R,5S)-3-[(4R,5R)-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl]-5-phenylpyrrolidine-2,4-dicarboxylate
• CAS: 135212-34-9
• 化学式: C₃₁H₃₅N₃O₄
• 分子量: 513.637
• InChiKey: MZTWTNVWBQTOHF-BXZOIBFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  71.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl (2R,3R,4R,5S)-3-[(4R,5R)-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl]-5-phenylpyrrolidine-2,4-dicarboxylate 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 1.5h， 以93%的产率得到dimethyl (2R,3R,4R,5S)-3-[(4R,5R)-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl]-1-(4-methylphenyl)sulfonyl-5-phenylpyrrolidine-2,4-dicarboxylate
  参考文献：
  名称：

  Diastereoselective cycloaddition of N-lithiated azomethine ylides to (E)-.alpha.,.beta.-unsaturated esters bearing a C2-symmetric imidazolidine chiral controller

  摘要：

  The 1,3-dipolar cycloaddition of N-metalated azomethine ylides to chiral (E)-3-(1,3-disubstituted 4,5-diphenylimidazolidin-2-yl)propenoates proceeded highly diastereoselectively. The previously unknown absolute configuration of optically pure 1,2-dianilino-1,2-diphenylethane was determined from the absolute configuration of the cycloadducts. What diastereotopic olefin face of the alpha,beta-unsaturated ester was attacked by the ylide was found to depend dramatically upon the nature of N substituents of the chiral controller as well as upon the bulkiness of the ester moiety of the ylide.

  DOI：

  10.1021/jo00014a028
• 作为产物：
  描述：

  Diethyl (1R,2R)-N,N'-(1,2-diphenylethylene)biscarbamate 在 甲醇 、 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 0.17h， 生成 dimethyl (2R,3R,4R,5S)-3-[(4R,5R)-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl]-5-phenylpyrrolidine-2,4-dicarboxylate
  参考文献：
  名称：

  Diastereoselective cycloaddition of N-lithiated azomethine ylides to (E)-.alpha.,.beta.-unsaturated esters bearing a C2-symmetric imidazolidine chiral controller

  摘要：

  The 1,3-dipolar cycloaddition of N-metalated azomethine ylides to chiral (E)-3-(1,3-disubstituted 4,5-diphenylimidazolidin-2-yl)propenoates proceeded highly diastereoselectively. The previously unknown absolute configuration of optically pure 1,2-dianilino-1,2-diphenylethane was determined from the absolute configuration of the cycloadducts. What diastereotopic olefin face of the alpha,beta-unsaturated ester was attacked by the ylide was found to depend dramatically upon the nature of N substituents of the chiral controller as well as upon the bulkiness of the ester moiety of the ylide.

  DOI：

  10.1021/jo00014a028

文献信息

• Diastereoselective cycloaddition of N-lithiated azomethine ylides to (E)-.alpha.,.beta.-unsaturated esters bearing a C2-symmetric imidazolidine chiral controller
  作者：Shuji Kanemasa、Takeshi Hayashi、Junji Tanaka、Hidetoshi Yamamoto、Tosio Sakurai

  DOI：10.1021/jo00014a028

  日期：1991.7

  The 1,3-dipolar cycloaddition of N-metalated azomethine ylides to chiral (E)-3-(1,3-disubstituted 4,5-diphenylimidazolidin-2-yl)propenoates proceeded highly diastereoselectively. The previously unknown absolute configuration of optically pure 1,2-dianilino-1,2-diphenylethane was determined from the absolute configuration of the cycloadducts. What diastereotopic olefin face of the alpha,beta-unsaturated ester was attacked by the ylide was found to depend dramatically upon the nature of N substituents of the chiral controller as well as upon the bulkiness of the ester moiety of the ylide.