(1S),(1'S)-N,N'-bis[1-(diphenylphosphinomethyl)-2-methylpropyl]succinylamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1S),(1'S)-N,N'-bis[1-(diphenylphosphinomethyl)-2-methylpropyl]succinylamide
• 英文别名: N,N'-bis[(2S)-1-diphenylphosphanyl-3-methylbutan-2-yl]butanediamide
• 化学式: C₃₈H₄₆N₂O₂P₂
• 分子量: 624.743
• InChiKey: OHJKNUZTCYFEPI-LQFQNGICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-2-(N-tert-butoxycarbonylamino)-3-methylbutyl tosylate 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (1S),(1'S)-N,N'-bis[1-(diphenylphosphinomethyl)-2-methylpropyl]succinylamide
  参考文献：
  名称：

  A new class of C2-symmetric diphosphine ligands derived from valine: remarkably diverse behavior in catalytic asymmetric transformations

  摘要：

  A new C-2-symmetric diphosphine ligand 8a was readily prepared in one step by treatment of the synthetic precursor of VALAP, 7, with phthaloyl chloride. Remarkably high levels of asymmetric induction, over 99% ee, were achieved using 8a in palladium-catalyzed asymmetric allylic transformations of sterically less demanding cyclohexenyl substrates 9. The ligand system was easily extended to the development of analogous chiral auxiliaries 8b,c by the identical procedure but using isophthaloyl chloride and succinyl chloride. However, the ligands 8b,c exhibited much lower catalytic activity. In contrast to the asymmetric allylic substitutions, Sc demonstrated significant improvement of enantioselectivity, up to 64% ee, in rhodium-catalyzed asymmetric hydrosilylations of acetophenone 11a compared to 35% ee using 8a. In this way, the versatility of the present ligand system played an important role in variations of substrates and reaction types. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00520-0

文献信息

• A new class of C2-symmetric diphosphine ligands derived from valine: remarkably diverse behavior in catalytic asymmetric transformations
  作者：Akihito Saitoh、Takashi Uda、Toshiaki Morimoto

  DOI：10.1016/s0957-4166(99)00520-0

  日期：1999.12

  A new C-2-symmetric diphosphine ligand 8a was readily prepared in one step by treatment of the synthetic precursor of VALAP, 7, with phthaloyl chloride. Remarkably high levels of asymmetric induction, over 99% ee, were achieved using 8a in palladium-catalyzed asymmetric allylic transformations of sterically less demanding cyclohexenyl substrates 9. The ligand system was easily extended to the development of analogous chiral auxiliaries 8b,c by the identical procedure but using isophthaloyl chloride and succinyl chloride. However, the ligands 8b,c exhibited much lower catalytic activity. In contrast to the asymmetric allylic substitutions, Sc demonstrated significant improvement of enantioselectivity, up to 64% ee, in rhodium-catalyzed asymmetric hydrosilylations of acetophenone 11a compared to 35% ee using 8a. In this way, the versatility of the present ligand system played an important role in variations of substrates and reaction types. (C) 1999 Elsevier Science Ltd. All rights reserved.