dimethyl (2R,3R,4R,5S)-1-(4-methylphenyl)sulfonyl-5-phenyl-3-[(4S,5S)-1,3,4,5-tetraphenylimidazolidin-2-yl]pyrrolidine-2,4-dicarboxylate | 135075-69-3

• 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)-1-(4-methylphenyl)sulfonyl-5-phenyl-3-[(4S,5S)-1,3,4,5-tetraphenylimidazolidin-2-yl]pyrrolidine-2,4-dicarboxylate
• CAS: 135075-69-3
• 化学式: C₄₈H₄₅N₃O₆S
• 分子量: 791.968
• InChiKey: KEMYZSPZTZDLIG-UKMVZYENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  58
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲醇 、 dimethyl (2R,3R,4R,5S)-1-(4-methylphenyl)sulfonyl-5-phenyl-3-[(4S,5S)-1,3,4,5-tetraphenylimidazolidin-2-yl]pyrrolidine-2,4-dicarboxylate 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以80%的产率得到dimethyl (2R,3R,4R,5S)-3-(dimethoxymethyl)-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：

  (1S,2S)-(-)-1,2-Dianilino-1,2-diphenylethane 在 甲醇 、 对甲苯磺酸 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 dimethyl (2R,3R,4R,5S)-1-(4-methylphenyl)sulfonyl-5-phenyl-3-[(4S,5S)-1,3,4,5-tetraphenylimidazolidin-2-yl]pyrrolidine-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.