(4R,5S)-ethyl 4-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-5-phenyl-2-thioxooxazolidine-5-carboxylate | 1219925-62-8

• 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)-ethyl 4-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-5-phenyl-2-thioxooxazolidine-5-carboxylate
• 英文别名: ethyl (4R,5S)-4-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-5-phenyl-2-thioxooxazolidine-5-carboxylate；ethyl (4R,5S)-4-(4,4-dimethyl-2-oxo-1,3-oxazolidine-3-carbonyl)-5-phenyl-2-sulfanylidene-1,3-oxazolidine-5-carboxylate
• CAS: 1219925-62-8
• 化学式: C₁₈H₂₀N₂O₆S
• 分子量: 392.433
• InChiKey: OWMTZWCDPZEHQS-SGTLLEGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  苯甲酰甲酸乙酯 、 3-(2-isothiocyanatoacetyl)-4,4-dimethyloxazolidin-2-one 在 1-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-3-((1R,2R)-2-(pyrrolidin-1-yl)cyclohexyl)thiourea 作用下， 以 甲苯 为溶剂， 反应 2.5h， 生成 (4R,5S)-ethyl 4-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-5-phenyl-2-thioxooxazolidine-5-carboxylate
  参考文献：
  名称：

  Direct Organocatalytic Asymmetric Aldol Reaction of α-Isothiocyanato Imides to α-Ketoesters under Low Ligand Loading: A Doubly Stereocontrolled Approach to Cyclic Thiocarbamates Bearing Chiral Quaternary Stereocenters

  摘要：

  The first doubly stereocontrolled organocatalytic asymmetric aldol reaction of alpha-isothiocyanato imides with alpha-ketoesters by using rosin-derived tertiary amine-thiourea under low ligand loading to form cyclic thiocarbamates bearing quaternary stereogenic centers with high levels of enantio- and diastereoselectivity (up to 99% ee, and 97:3 dr) is presented. This reaction provides a convenient doubly stereocontrolled method to access synthetic useful multiply substituted cyclic thiocarbamates with high optical purity.

  DOI：

  10.1021/ol1002829

文献信息

• Catalytic enantioselective aldol additions of α-isothiocyanato imides to α-ketoesters
  作者：Matthew K. Vecchione、Le Li、Daniel Seidel

  DOI：10.1039/c0cc00556h

  日期：——

  A readily available bifunctional thiourea catalyst promotes aldol additions of alpha-isothiocyanato imides to alpha-ketoesters under mild reaction conditions to form beta-hydroxy-alpha-amino acid derivatives with high levels of enantioselectivity.

  容易获得的双官能硫脲催化剂在温和的反应条件下促进α-异硫氰基酰亚胺向α-酮酸酯的醇醛加成反应，以形成具有高对映选择性的β-羟基-α-氨基酸衍生物。