(3SR,4SR)-[(1'RS,2'SR)-(2'-hydroxy-2'-phenyl-1'-vinyl)ethyl]-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

• 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: (3SR,4SR)-[(1'RS,2'SR)-(2'-hydroxy-2'-phenyl-1'-vinyl)ethyl]-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol
• 英文别名: (3S,4S)-4-[(1S,2R)-1-hydroxy-1-phenylbut-3-en-2-yl]-1-(4-methylphenyl)sulfonylpyrrolidin-3-ol
• 化学式: C₂₁H₂₅NO₄S
• 分子量: 387.5
• InChiKey: AUYJOSKVVWGOJO-XRXFAXGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲醛 、 4-Methyl-N-(2-oxo-ethyl)-N-((E)-penta-2,4-dienyl)-benzenesulfonamide 在 bis(1,5-cyclooctadiene)nickel (0) 、 三(2-呋喃基)膦 、 联硼酸新戊二醇酯 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以77%的产率得到(3SR,4SR)-[(1'RS,2'SR)-(2'-hydroxy-2'-phenyl-1'-vinyl)ethyl]-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol
  参考文献：
  名称：

  A Highly Stereoselective Sequential Allylic Transfer Reaction of Diene with Diboronyl Reagent and Aldehydes Promoted by Nickel Catalyst

  摘要：

  graph A new protocol for the sequential allylic transfer reaction of a diene with two aldehydes in the construction of cyclic systems containing four stereogenic centers is achieved in a one-pot operation. Reaction of the diene-alehyde 1 with aldehyde in the presence of the diboronyl reagent catalyzed by a nickel complex produces products 2 and 3 depending on reaction conditions in high levels of diastereoselectivity. Extension of this method to the synthesis of six-membered rings is also investigated.

  DOI：

  10.1021/ol051806c

文献信息

• A Highly Stereoselective Sequential Allylic Transfer Reaction of Diene with Diboronyl Reagent and Aldehydes Promoted by Nickel Catalyst
  作者：Chan-Mo Yu、Jinsuop Youn、Seok-Keun Yoon、Young-Tack Hong

  DOI：10.1021/ol051806c

  日期：2005.9.1

  graph A new protocol for the sequential allylic transfer reaction of a diene with two aldehydes in the construction of cyclic systems containing four stereogenic centers is achieved in a one-pot operation. Reaction of the diene-alehyde 1 with aldehyde in the presence of the diboronyl reagent catalyzed by a nickel complex produces products 2 and 3 depending on reaction conditions in high levels of diastereoselectivity. Extension of this method to the synthesis of six-membered rings is also investigated.