(4R,5S)-4-(methoxycarbonyl)-5-phenyl-N-tosyl-2-imidazoline | 1066717-17-6

• 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: (4R,5S)-4-(methoxycarbonyl)-5-phenyl-N-tosyl-2-imidazoline
• 英文别名: methyl (4R,5S)-1-(4-methylphenyl)sulfonyl-5-phenyl-4,5-dihydroimidazole-4-carboxylate
• CAS: 1066717-17-6
• 化学式: C₁₈H₁₈N₂O₄S
• 分子量: 358.418
• InChiKey: XNEIKJUGWXHQSU-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-亚苄基-4-甲基苯磺酰胺 、 异腈基乙酸甲酯 在 (S)-(6-hydroxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl acetate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 methyl 1-[(4-methylphenyl)sulfonyl]-5-phenyl-4,5-dihydro-1H-4-imidazolecarboxylate 、 methyl 1-[(4-methylphenyl)sulfonyl]-5-phenyl-4,5-dihydro-1H-4-imidazolecarboxylate 、 (4R,5S)-4-(methoxycarbonyl)-5-phenyl-N-tosyl-2-imidazoline 、 (4S,5S)-4-(methoxycarbonyl)-5-phenyl-N-tosyl-2-imidazoline
  参考文献：
  名称：

  Organocatalytic asymmetric Mannich-type reaction of N-sulfonylimines with isocyanoacetate leading to optically active 2-imidazoline-4-carboxylates

  摘要：

  The first asymmetric Mannich-type reaction of methyl isocyanoacetate with N-sulfonylimines catalyzed by cinchona alkaloid derivatives yielded 2-imidazolines with high diastereoselectivities and good enantioselectivities (up to >99:1 dr and 70% ee). This reaction provided a convenient route to access various substituted 2-imidazoline-4-carboxylates and related alpha,beta-diamino acids in high enantiomeric purities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.029

文献信息

• Chiral palladium-pincer complex catalyzed asymmetric condensation of sulfonimines and isocyanoacetate
  作者：Juhanes Aydin、Andreas Rydén、Kálmán J. Szabó

  DOI：10.1016/j.tetasy.2008.07.027

  日期：2008.8

  The asymmetric condensation of isocyanoacetate and sulfonimines was studied. Chiral BINOL and biphenantrol-based palladium-pincer complexes proved to be efficient catalysts affording 2-imidazoline derivatives with up to 86% ee. The level of enantioselectivity was clearly dependent on the gamma-substituents of the BINOL ring. The best results were obtained by using biphenantrol-based pincer-complex catalysts. Some of the complexes induced the selective formation of the anti-diastereorner of the 2-imidazoline. The diastereo- and enantioselectivity showed an interesting solvent dependence as well. It was found that the application of diglyme as a solvent instead of THF leads to preferential formation of the anti product with a slight decrease of the enantioselectivity. (C) 2008 Elsevier Ltd. All rights reserved.
• Organocatalytic asymmetric Mannich-type reaction of N-sulfonylimines with isocyanoacetate leading to optically active 2-imidazoline-4-carboxylates
  作者：Zhen-Wei Zhang、Gui Lu、Miao-Miao Chen、Ning Lin、Yong-Bo Li、Tamio Hayashi、Albert S.C. Chan

  DOI：10.1016/j.tetasy.2010.04.029

  日期：2010.7

  The first asymmetric Mannich-type reaction of methyl isocyanoacetate with N-sulfonylimines catalyzed by cinchona alkaloid derivatives yielded 2-imidazolines with high diastereoselectivities and good enantioselectivities (up to >99:1 dr and 70% ee). This reaction provided a convenient route to access various substituted 2-imidazoline-4-carboxylates and related alpha,beta-diamino acids in high enantiomeric purities. (C) 2010 Elsevier Ltd. All rights reserved.