tert-butyl (2R,3R)-3-hydroxy-2-methyl-5-phenylpentanoate | 1137584-04-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: tert-butyl (2R,3R)-3-hydroxy-2-methyl-5-phenylpentanoate
• CAS: 1137584-04-3
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: SVKDSPBPBJPXKE-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙烯酸叔丁酯 以 乙醚 为溶剂， 反应 20.0h， 生成 tert-butyl (2R,3R)-3-hydroxy-2-methyl-5-phenylpentanoate 、 tert-butyl (2S,3S)-3-hydroxy-2-methyl-5-phenylpentanoate
  参考文献：
  名称：

  (Diisopinocampheyl)borane-Mediated Reductive Aldol Reactions of Acrylate Esters: Enantioselective Synthesis of Anti-Aldols

  摘要：

  The (diisopinocampheyl)borane promoted reductive aldol reaction of acrylate esters 4 is described. Isomerization of the kinetically formed Z(O)-enolborinate 5Z to the thermodynamic E(O)-enolborinate 5E via 1,3-boratropic shifts, followed by treatment with representative achiral aldehydes, leads to anti-alpha-methyl-beta-hydroxy esters 9 or 10 with excellent diastereo- (up to >= 20:1 dr) and enantioselectivity (up to 87% ee). The results of double asymmetric reactions of 5E with several chiral aldehydes are also presented.

  DOI：

  10.1021/ol401679g

文献信息

• Asymmetric Aldol Reaction with Diisopinocampheyl Enolborinates of Propionates
  作者：P. Veeraraghavan Ramachandran、Debarshi Pratihar

  DOI：10.1021/ol802850w

  日期：2009.4.2

  A convenient and general, reagent-controlled, diastereo- and enantioselective aldol reaction of diisopinocampheylboron enolates of esters, followed by reduction, has been developed as an alternative to crotylboration-ozonolysis. This protocol was then exploited for the double diastereoselective synthesis of the C11-C17 subunit of (-)-dictyostatin.