(4R,5S)-methyl 4-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-5-(4-fluorophenyl)-2-thioxooxazolidine-5-carboxylate | 1219925-48-0

• 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)-methyl 4-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-5-(4-fluorophenyl)-2-thioxooxazolidine-5-carboxylate
• CAS: 1219925-48-0
• 化学式: C₁₇H₁₇FN₂O₆S
• 分子量: 396.396
• InChiKey: RWQJPKGCPSFRLC-GTNSWQLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  94.17
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  3-(2-isothiocyanatoacetyl)-4,4-dimethyloxazolidin-2-one 、 methyl (p-fluorobenzoyl)formate 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 2.67h， 生成 (4R,5S)-methyl 4-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-5-(4-fluorophenyl)-2-thioxooxazolidine-5-carboxylate 、 (4RS,5RS)-methyl 4-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-5-(4-fluorophenyl)-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