3,4-bis[(2'R,5'S)-3'-phenyl-1',3'-diaza-2'-phosphabicyclo[3.3.0]octyloxy]-(3R,4R)-1-benzylpyrrolidine-2,5-dione | 1136222-67-7

• 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: 3,4-bis[(2'R,5'S)-3'-phenyl-1',3'-diaza-2'-phosphabicyclo[3.3.0]octyloxy]-(3R,4R)-1-benzylpyrrolidine-2,5-dione
• 英文别名: (3R,4R)-3,4-bis[[(1R,3aS)-2-phenyl-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]diazaphosphol-1-yl]oxy]-1-benzylpyrrolidine-2,5-dione
• CAS: 1136222-67-7
• 化学式: C₃₃H₃₇N₅O₄P₂
• 分子量: 629.635
• InChiKey: IHHGZMBEAOVUTM-IUWZMZCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (+/-)-1-benzyl-3r,4t-dihydroxy-pyrrolidine-2,5-dione 、 (3aS)-1-chloro-2-phenyl-hexahydro-1H-pyrrolo[1,2-c][1,3,2]diazaphosphole 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到3,4-bis[(2'R,5'S)-3'-phenyl-1',3'-diaza-2'-phosphabicyclo[3.3.0]octyloxy]-(3R,4R)-1-benzylpyrrolidine-2,5-dione
  参考文献：
  名称：

  P∗,P∗-Bidentate diastereoisomeric bisdiamidophosphites based on N-benzyltartarimide and their applications in asymmetric catalytic processes

  摘要：

  Two novel P*-stereogenic bisdiamidophosphites derived from (3R,4R)-N-benzyltartarimide as a chiral 1,2-diol have been prepared from readily available starting materials. Palladium and rhodium catalytic systems containing these new P*,P*-bidentate ligands afforded 96%, 83% and 65% ee in asymmetric allylic substitution, hydrogenation and addition processes, respectively. These diastereomeric diamidophosphites were found to be complementary stereoselectors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.022
• 作为试剂：
  描述：

  1-(ethoxycarbonyloxy)-2-cyclohexene 、 丙二酸二甲酯 在 N,O-双三甲硅基乙酰胺 、 bis(η3-allyl-μ-chloropalladium(II)) 、 3,4-bis[(2'R,5'S)-3'-phenyl-1',3'-diaza-2'-phosphabicyclo[3.3.0]octyloxy]-(3R,4R)-1-benzylpyrrolidine-2,5-dione 、 potassium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 dimethyl 2-(cyclohex-2-en-1-yl)propanedioate 、 (S)-dimethyl 2-(cyclohex-2-enyl)malonate
  参考文献：
  名称：

  P∗,P∗-Bidentate diastereoisomeric bisdiamidophosphites based on N-benzyltartarimide and their applications in asymmetric catalytic processes

  摘要：

  Two novel P*-stereogenic bisdiamidophosphites derived from (3R,4R)-N-benzyltartarimide as a chiral 1,2-diol have been prepared from readily available starting materials. Palladium and rhodium catalytic systems containing these new P*,P*-bidentate ligands afforded 96%, 83% and 65% ee in asymmetric allylic substitution, hydrogenation and addition processes, respectively. These diastereomeric diamidophosphites were found to be complementary stereoselectors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.022

文献信息

• P∗,P∗-Bidentate diastereoisomeric bisdiamidophosphites based on N-benzyltartarimide and their applications in asymmetric catalytic processes
  作者：Konstantin N. Gavrilov、Sergey V. Zheglov、Eduard B. Benetsky、Anton S. Safronov、Eugenie A. Rastorguev、Nikolay N. Groshkin、Vadim A. Davankov、Benjamin Schäffner、Armin Börner

  DOI：10.1016/j.tetasy.2009.10.022

  日期：2009.11

  Two novel P*-stereogenic bisdiamidophosphites derived from (3R,4R)-N-benzyltartarimide as a chiral 1,2-diol have been prepared from readily available starting materials. Palladium and rhodium catalytic systems containing these new P*,P*-bidentate ligands afforded 96%, 83% and 65% ee in asymmetric allylic substitution, hydrogenation and addition processes, respectively. These diastereomeric diamidophosphites were found to be complementary stereoselectors. (C) 2009 Elsevier Ltd. All rights reserved.