(2R,4S,5R)-methyl 5-((benzyloxy)methyl)-4-(phenylsulfonyl)pyrrolidine-2-carboxylate | 1574387-81-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,4S,5R)-methyl 5-((benzyloxy)methyl)-4-(phenylsulfonyl)pyrrolidine-2-carboxylate
• 英文别名: methyl (2R,4S,5R)-4-(benzenesulfonyl)-5-(phenylmethoxymethyl)pyrrolidine-2-carboxylate
• CAS: 1574387-81-7
• 化学式: C₂₀H₂₃NO₅S
• 分子量: 389.472
• InChiKey: MVZZNRPIJAJYPS-QRVBRYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲醇 、 苯基乙烯基砜 、 甲酸苄酯 、 2-amino-1-(1,1-dioxidobenzo[d]isothiazol-2(3H)-yl)ethanone 在 (S)-(+)-5,5'-双[二(3,5-二叔丁基-4-甲氧基苯基)膦]-4,4'-二-1,3-苯并二氧戊环 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 dipotassium hydrogenphosphate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以81%的产率得到(2R,4S,5R)-methyl 5-((benzyloxy)methyl)-4-(phenylsulfonyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Catalytic Asymmetric Exo-Selective [C+NC+CC] Reaction

  摘要：

  A catalytic asymmetric version of the exoselective [C+NC+CC] reaction is reported. This multicomponent reaction utilizes a readily prepared achiral glycyl sultam as the "NC" component and commercially available catalyst components. The method can be applied to a variety of aldehydes ("C" component) and activated alkenes ("CC" component) to provide substituted pyrrolidines in good yields and high enantioselectivities. Of particular note is the ability to employ labile enolizable aldehydes (e.g., acetaldehyde and propionaldehyde) in this reaction.

  DOI：

  10.1021/ol500474a

文献信息

• Catalytic Asymmetric <i>Exo</i>-Selective [C+NC+CC] Reaction
  作者：Ryan Joseph、Charles Murray、Philip Garner

  DOI：10.1021/ol500474a

  日期：2014.3.21

  A catalytic asymmetric version of the exoselective [C+NC+CC] reaction is reported. This multicomponent reaction utilizes a readily prepared achiral glycyl sultam as the "NC" component and commercially available catalyst components. The method can be applied to a variety of aldehydes ("C" component) and activated alkenes ("CC" component) to provide substituted pyrrolidines in good yields and high enantioselectivities. Of particular note is the ability to employ labile enolizable aldehydes (e.g., acetaldehyde and propionaldehyde) in this reaction.