(2R,3R)-methyl 2-formylamino-3-[(4-methylphenyl)sulfonyl]amino-3-phenylpropanoate | 1066717-33-6

• 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: (2R,3R)-methyl 2-formylamino-3-[(4-methylphenyl)sulfonyl]amino-3-phenylpropanoate
• CAS: 1066717-33-6
• 化学式: C₁₈H₂₀N₂O₅S
• 分子量: 376.433
• InChiKey: BWHOJYVUZGHRBE-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  101.57
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  methyl 1-[(4-methylphenyl)sulfonyl]-5-phenyl-4,5-dihydro-1H-4-imidazolecarboxylate 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (2S,3R)-methyl 2-formylamino-3-[(4-methylphenyl)sulfonyl]amino-3-phenylpropanoate 、 (2R,3R)-methyl 2-formylamino-3-[(4-methylphenyl)sulfonyl]amino-3-phenylpropanoate 、 (2S,3S)-methyl 2-formylamino-3-[(4-methylphenyl)sulfonyl]amino-3-phenylpropanoate 、 (2R,3S)-methyl 2-formylamino-3-[(4-methylphenyl)sulfonyl]amino-3-phenylpropanoate
  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.