(R)-2-((1,3-bis(naphthalen-1-ylmethyl)-2-oxido-1,3,2-diazaphospholidin-2-yl)amino)-2-phenylacetonitrile | 1238201-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-((1,3-bis(naphthalen-1-ylmethyl)-2-oxido-1,3,2-diazaphospholidin-2-yl)amino)-2-phenylacetonitrile
• CAS: 1238201-15-4
• 化学式: C₃₂H₂₉N₄OP
• 分子量: 516.582
• InChiKey: ZYEFPOBTOBMGQG-YTTGMZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.27
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  59.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-[1,3-bis(naphthalen-1-ylmethyl)-2-oxo-1,3,2lambda5-diazaphospholidin-2-yl]-1-phenylmethanimine 、 二乙基氰化铝 在 D-缬氨酸 、 异丙醇 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 (2S)-2-[[1,3-bis(naphthalen-1-ylmethyl)-2-oxo-1,3,2lambda5-diazaphospholidin-2-yl]amino]-2-phenylacetonitrile 、 (R)-2-((1,3-bis(naphthalen-1-ylmethyl)-2-oxido-1,3,2-diazaphospholidin-2-yl)amino)-2-phenylacetonitrile
  参考文献：
  名称：

  Asymmetric Catalytic N-Phosphonyl Imine Chemistry: The Use of Primary Free Amino Acids and Et₂AlCN for Asymmetric Catalytic Strecker Reaction

  摘要：

  The new asymmetric catalytic Strecker reaction of achiral N-phosphonyl imines has been established. Excellent enantioselectivity (95.2-99.7% ee) and yields (89-97%) have been achieved by using primary free natural amino acids as catalysts and Et2AlCN as nucleophile. This work also presents the novel use of nonvolatile and inexpensive Et2AlCN in asymmetric catalysis. The N-phosphonyl protecting group enabled simple product purification to be achieved simply by washing the crude products with hexane, which is defined as the GAP chemistry (GAP: Group-Assistant-Purification).(15) It can also be readily cleaved and recycled under mild condition to give a quantitative recovery of N,N'-bis(naphthalen-1-ylmethyl)ethane-1,2-diamine. A new mechanism was proposed for this reaction and was supported by experimental observations.

  DOI：

  10.1021/jo100865q

文献信息

• Asymmetric catalytic Strecker reaction of N-phosphonyl imines with Et2AlCN using amino alcohols and BINOLs as catalysts
  作者：Parminder Kaur、Suresh Pindi、Walter Wever、Trideep Rajale、Guigen Li

  DOI：10.1039/c0cc00287a

  日期：——

  The asymmetric catalytic Strecker reaction of achiral N-phosphonyl imines with Et2AlCN has been established. Both free amino alcohols and BINOLs have been proven to be effective catalysts to afford excellent enantioselectivities and yields. The N-phosphonyl group can be readily cleaved under mild conditions and enable purification of crude products by simple washing with hexane. The cleaved N,N-dialkyl diamine auxiliary can be recovered quantitatively via n-BuOH extraction. The scope for both N-phosphonyl imines and catalysts was vastly studied for this new catalytic system.

  建立了非手性 N-膦酰亚胺与 Et2AlCN 的不对称催化 Strecker 反应。游离氨基醇和联醇已被证明是有效的催化剂，可提供优异的对映选择性和产率。 N-膦酰基可以在温和条件下容易地裂解，并且可以通过用己烷简单洗涤来纯化粗产物。裂解的 N,N-二烷基二胺辅助剂可以通过正丁醇萃取定量回收。对于这种新的催化体系，对 N-膦酰亚胺和催化剂的范围进行了广泛的研究。