(2R,3S)-3-tert-butoxy-1-(trimethylsilyloxy)-pyrrolidine-2-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,3S)-3-tert-butoxy-1-(trimethylsilyloxy)-pyrrolidine-2-carbonitrile
• 英文别名: (2R,3S)-3-[(2-methylpropan-2-yl)oxy]-1-trimethylsilyloxypyrrolidine-2-carbonitrile
• 化学式: C₁₂H₂₄N₂O₂Si
• 分子量: 256.42
• InChiKey: IDRAAUVYFKHAQJ-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-tert-butoxy-1-(trimethylsilyloxy)-pyrrolidine-2-carbonitrile 在 柠檬酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到(2R,3S)-3-tert-butoxy-1-hydroxypyrrolidine-2-carbonitrile
  参考文献：
  名称：

  A comparative study of the stereoselective addition of trimethylsilyl cyanide and diethylaluminum cyanide to chiral cyclic nitrones

  摘要：

  The mild cyanating agent trimethylsilyl cyanide adds with total stereo selectivity to alpha-alkoxy cyclic nitrones to afford the corresponding trans-hydroxyaminonitriles. The addition of Lewis acids to precomplexing the nitrones does not affect the stereoselectivity of these additions significantly. In all of the cases examined, excellent yields of diastereomerically homogeneous products were obtained. On the other hand, the use of diethylaluminum cyanide as cyanating agent leads to low diastereoselectivities. Both NMR studies and theoretical calculations show that whereas the addition of trimethylsilyl cyanide takes place through a concerted mechanism, in the addition of diethylaluminum cyanide, a complex is formed prior to the intramolecular delivery of the cyanide ion. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00832-7
• 作为产物：
  描述：

  三甲基氰硅烷 、 (4S)-4-tert-butoxy-3,4-dihydro-2H-pyrrole 1-oxide 以 二氯甲烷 为溶剂， 反应 16.0h， 以100%的产率得到(2R,3S)-3-tert-butoxy-1-(trimethylsilyloxy)-pyrrolidine-2-carbonitrile
  参考文献：
  名称：

  A comparative study of the stereoselective addition of trimethylsilyl cyanide and diethylaluminum cyanide to chiral cyclic nitrones

  摘要：

  The mild cyanating agent trimethylsilyl cyanide adds with total stereo selectivity to alpha-alkoxy cyclic nitrones to afford the corresponding trans-hydroxyaminonitriles. The addition of Lewis acids to precomplexing the nitrones does not affect the stereoselectivity of these additions significantly. In all of the cases examined, excellent yields of diastereomerically homogeneous products were obtained. On the other hand, the use of diethylaluminum cyanide as cyanating agent leads to low diastereoselectivities. Both NMR studies and theoretical calculations show that whereas the addition of trimethylsilyl cyanide takes place through a concerted mechanism, in the addition of diethylaluminum cyanide, a complex is formed prior to the intramolecular delivery of the cyanide ion. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00832-7

文献信息

• A comparative study of the stereoselective addition of trimethylsilyl cyanide and diethylaluminum cyanide to chiral cyclic nitrones
  作者：Pedro Merino、Tomas Tejero、Julia Revuelta、Pilar Romero、Stefano Cicchi、Vanni Mannucci、Alberto Brandi、Andrea Goti

  DOI：10.1016/s0957-4166(02)00832-7

  日期：2003.2

  The mild cyanating agent trimethylsilyl cyanide adds with total stereo selectivity to alpha-alkoxy cyclic nitrones to afford the corresponding trans-hydroxyaminonitriles. The addition of Lewis acids to precomplexing the nitrones does not affect the stereoselectivity of these additions significantly. In all of the cases examined, excellent yields of diastereomerically homogeneous products were obtained. On the other hand, the use of diethylaluminum cyanide as cyanating agent leads to low diastereoselectivities. Both NMR studies and theoretical calculations show that whereas the addition of trimethylsilyl cyanide takes place through a concerted mechanism, in the addition of diethylaluminum cyanide, a complex is formed prior to the intramolecular delivery of the cyanide ion. (C) 2003 Elsevier Science Ltd. All rights reserved.