(4S,5R)-3-[{(2'S)-(1'-benzyloxycarbonyl)aziridin-2'-yl}carbonyl]-4,5-diphenyl-2-oxazolidinone | 1314042-72-2

• 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: (4S,5R)-3-[{(2'S)-(1'-benzyloxycarbonyl)aziridin-2'-yl}carbonyl]-4,5-diphenyl-2-oxazolidinone
• 英文别名: benzyl (2S)-2-[(4S,5R)-2-oxo-4,5-diphenyl-1,3-oxazolidine-3-carbonyl]aziridine-1-carboxylate
• CAS: 1314042-72-2
• 化学式: C₂₆H₂₂N₂O₅
• 分子量: 442.471
• InChiKey: IQIFVFFDUWYUBN-BYVVOIMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  75.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (4S,5R)-(?)-顺-4,5-二苯基-2-噁唑烷酮 在 Br^(1-)*C₃₇H₃₇N₂O⁽¹⁺⁾ 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (4S,5R)-3-[{(2'S)-(1'-benzyloxycarbonyl)aziridin-2'-yl}carbonyl]-4,5-diphenyl-2-oxazolidinone 、 (4S,5R)-3-[{(2'R)-(1'-benzyloxycarbonyl)aziridin-2'-yl}carbonyl]-4,5-diphenyl-2-oxazolidinone
  参考文献：
  名称：

  Diastereoselective Aziridination of Chiral Electron-Deficient Olefins with N-Chloro-N-sodiocarbamates Catalyzed by Chiral Quaternary Ammonium Salts

  摘要：

  Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the "matching" stereochemical combination of chiral auxiliary/ammonium salt. For example, when 3-phenyl-(4R,7S)-4-methyl-7-isopropyl-4,S,6,7-tetrahydroindazole (L-menthopyrazole) as a chiral auxiliary and a cinchonidine-derived chiral ammonium salt as a catalyst were applied to the reaction system, perfect diastereoselectivity was realized. Furthermore, the preparation of enantiomerically pure aziridines by removal of the chiral auxiliary was demonstrated.

  DOI：

  10.1021/jo2010632

文献信息

• Diastereoselective Aziridination of Chiral Electron-Deficient Olefins with <i>N</i>-Chloro-<i>N</i>-sodiocarbamates Catalyzed by Chiral Quaternary Ammonium Salts
  作者：Yuta Murakami、Youhei Takeda、Satoshi Minakata

  DOI：10.1021/jo2010632

  日期：2011.8.5

  Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the "matching" stereochemical combination of chiral auxiliary/ammonium salt. For example, when 3-phenyl-(4R,7S)-4-methyl-7-isopropyl-4,S,6,7-tetrahydroindazole (L-menthopyrazole) as a chiral auxiliary and a cinchonidine-derived chiral ammonium salt as a catalyst were applied to the reaction system, perfect diastereoselectivity was realized. Furthermore, the preparation of enantiomerically pure aziridines by removal of the chiral auxiliary was demonstrated.