(2R,5S)-2-(S,S-diphenylsulfonimidoyl)-3,1,2-oxazaphosphabicyclo[3.3.0]-octane | 1312767-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,5S)-2-(S,S-diphenylsulfonimidoyl)-3,1,2-oxazaphosphabicyclo[3.3.0]-octane
• 英文别名: [(1R,3aS)-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaphosphol-1-yl]imino-oxo-diphenyl-lambda6-sulfane；[(1R,3aS)-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaphosphol-1-yl]imino-oxo-diphenyl-λ6-sulfane
• CAS: 1312767-73-9
• 化学式: C₁₇H₁₉N₂O₂PS
• 分子量: 346.39
• InChiKey: GEGAQZMAJDCQME-NYHFZMIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  S,S-diphenylsulphoximine 、 (2R,5S)-2-chloro-3,1-oxaza-2-phosphabicyclo[3.3.0]octane 在 三乙胺 作用下， 以 甲苯 为溶剂， 生成 (2R,5S)-2-(S,S-diphenylsulfonimidoyl)-3,1,2-oxazaphosphabicyclo[3.3.0]-octane 、 (2S,5S)-2-(S,S-diphenylsulfonimidoyl)-3,1,2-oxazaphosphabicyclo[3.3.0]-octane
  参考文献：
  名称：

  Synthesis of phosphorylated sulfoximines and sulfinamides and their application as ligands in asymmetric metal catalysis

  摘要：

  Starting from inexpensive materials and following simple protocols various N-phosphorylated sulfoximines and sulfinamides have been synthesized. The newly prepared compounds were then applied as chiral ligands in asymmetric transition metal catalysis. Phosphorus triamide-type ligands derived from (S)-glutamic acid were found to be the most efficient stereoselectors in enantioselective palladium-catalyzed allylic substitutions (up to 97% ee). On the other hand, diamidophosphite-type structures stemming from (S)-proline were the best ligands in rhodium-catalyzed hydrogenation reactions (up to 84% ee). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.005

文献信息

• Synthesis of phosphorylated sulfoximines and sulfinamides and their application as ligands in asymmetric metal catalysis
  作者：Eduard B. Benetskiy、Carsten Bolm

  DOI：10.1016/j.tetasy.2011.02.005

  日期：2011.2

  Starting from inexpensive materials and following simple protocols various N-phosphorylated sulfoximines and sulfinamides have been synthesized. The newly prepared compounds were then applied as chiral ligands in asymmetric transition metal catalysis. Phosphorus triamide-type ligands derived from (S)-glutamic acid were found to be the most efficient stereoselectors in enantioselective palladium-catalyzed allylic substitutions (up to 97% ee). On the other hand, diamidophosphite-type structures stemming from (S)-proline were the best ligands in rhodium-catalyzed hydrogenation reactions (up to 84% ee). (C) 2011 Elsevier Ltd. All rights reserved.