[(4S,5S)-(2-methyl-5-phenyl-2-oxazolin-4-yl)methoxy]bis(1-pyrrolyl)phosphinite | 892865-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: [(4S,5S)-(2-methyl-5-phenyl-2-oxazolin-4-yl)methoxy]bis(1-pyrrolyl)phosphinite
• CAS: 892865-26-8
• 化学式: C₁₉H₂₀N₃O₂P
• 分子量: 353.36
• InChiKey: YZVYEEBAFOIQJA-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.68
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(4S,5S)-(2-methyl-5-phenyl-2-oxazolin-4-yl)methoxy]bis(1-pyrrolyl)phosphinite 、 di(rhodium)tetracarbonyl dichloride 以 not given 为溶剂， 以90%的产率得到chloro([(4S,5S)-(2-methyl-5-phenyl-2-oxazolin-4-yl)methoxy]bis(1-pyrrolyl)phosphinite)carbonylrhodium(I)
  参考文献：
  名称：

  Imino‐ and Oxazolino‐Functionalised Pyrrolylphosphanes and Pyrrolylphosphinites: An Unexploited Class of Chiral P,N ‐Bidentate Ligands with Unusual Electronic Properties

  摘要：

  AbstractEnantiopure P,N‐bidentate pyrrolylphosphanes and pyrrolylphosphinites have been prepared based upon chiral imino‐ and oxazolino‐containing compounds. Complexation of the new ligands with [Rh(CO)2Cl]2 and [Pd(allyl)Cl]2 has been found to give the chelate complexes [Rh(CO)Cl(η2‐P,N)] and [Pd(allyl)(η2‐P,N)]+BF4–, respectively. Imino‐ and oxazolino‐functionalised pyrrolylphosphanes and pyrrolylphosphinites have been shown to be a novel class of P,N‐bidentate ligands possessing exceptional π‐acceptor and original σ‐donor properties. With these ligands, up to 77 % ee has been achieved in the asymmetric Pd‐catalyzed sulfonylation of 1,3‐diphenyl‐2‐propenyl acetate with sodium p‐toluenesulfinate. In the enantioselective alkylation of 1,3‐diphenyl‐2‐propenyl acetate with dimethyl malonate, up to 93 % enantioselectivity has been achieved by using [Pd(allyl)(η2‐P,N)]+BF4– complexes as chiral catalysts. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejic.200500075
• 作为产物：
  描述：

  (4S,5S)-(-)-2-甲基-5-苯基-2-恶唑啉-4-甲醇 、 4-氨基环己酮盐酸盐 在 三乙胺 作用下， 以 苯 为溶剂， 反应 0.5h， 以90%的产率得到[(4S,5S)-(2-methyl-5-phenyl-2-oxazolin-4-yl)methoxy]bis(1-pyrrolyl)phosphinite
  参考文献：
  名称：

  Imino‐ and Oxazolino‐Functionalised Pyrrolylphosphanes and Pyrrolylphosphinites: An Unexploited Class of Chiral P,N ‐Bidentate Ligands with Unusual Electronic Properties

  摘要：

  AbstractEnantiopure P,N‐bidentate pyrrolylphosphanes and pyrrolylphosphinites have been prepared based upon chiral imino‐ and oxazolino‐containing compounds. Complexation of the new ligands with [Rh(CO)2Cl]2 and [Pd(allyl)Cl]2 has been found to give the chelate complexes [Rh(CO)Cl(η2‐P,N)] and [Pd(allyl)(η2‐P,N)]+BF4–, respectively. Imino‐ and oxazolino‐functionalised pyrrolylphosphanes and pyrrolylphosphinites have been shown to be a novel class of P,N‐bidentate ligands possessing exceptional π‐acceptor and original σ‐donor properties. With these ligands, up to 77 % ee has been achieved in the asymmetric Pd‐catalyzed sulfonylation of 1,3‐diphenyl‐2‐propenyl acetate with sodium p‐toluenesulfinate. In the enantioselective alkylation of 1,3‐diphenyl‐2‐propenyl acetate with dimethyl malonate, up to 93 % enantioselectivity has been achieved by using [Pd(allyl)(η2‐P,N)]+BF4– complexes as chiral catalysts. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejic.200500075