(2S,4R)-1-benzyl-2-[diphenyl(trimethylsilyloxy)methyl]-4-(trimethylsilyloxy)pyrrolidine | 1262967-76-9

• 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: (2S,4R)-1-benzyl-2-[diphenyl(trimethylsilyloxy)methyl]-4-(trimethylsilyloxy)pyrrolidine
• CAS: 1262967-76-9
• 化学式: C₃₀H₄₁NO₂Si₂
• 分子量: 503.832
• InChiKey: OACNLUKVTKSYHE-WDYNHAJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  甲醇 、 三甲基氯硅烷 、 1-{2-[(3R,5S)-1-benzyl-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy]-2-oxoethyl}-3-methyl-1H-imidazol-3-ium iodide 在 5% Pd(II)/C(eggshell) 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 31.0h， 以62%的产率得到(2S,4R)-1-benzyl-2-[diphenyl(trimethylsilyloxy)methyl]-4-(trimethylsilyloxy)pyrrolidine
  参考文献：
  名称：

  α,α-Diarylprolinol-derived chiral ionic liquids: recoverable organocatalysts for the domino reaction between α,β-enals and N-protected hydroxylamines

  摘要：

  Chiral ionic liquids bearing alpha alpha-diarylprolinol units were synthesized and applied for the first time as organocatalysts for the domino reaction between alpha beta-enals and N-protected hydroxylamines involving aza-Michael and intramolecular acetalization steps Corresponding 5-hydroxy-3-arylisoxazolidines with either an (S)- or (R)-configuration at C-3 were obtained in excellent yields (up to 94%) and with moderate to high enantioselectivities (64 to >99% ee) The ionic liquid supported catalyst can be easily recycled and reused for at least four times without a significant loss of chemical yield or enantioselectivity (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.020