(E)-methyl 9-hydroxy-15-oxopentadec-13-enoate | 1346850-57-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-methyl 9-hydroxy-15-oxopentadec-13-enoate
• CAS: 1346850-57-4
• 化学式: C₁₆H₂₈O₄
• 分子量: 284.396
• InChiKey: ZVAIEHUZQDEQKI-UXBLZVDNSA-N

反应信息

• 作为反应物：
  描述：

  (E)-methyl 9-hydroxy-15-oxopentadec-13-enoate 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 4-二甲氨基吡啶 、 三乙胺 、 苯甲酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.58h， 生成 2-((2R,6R)-6-(8-methoxy-8-oxooctyl)tetrahydro-2H-pyran-2-yl)ethyl 4-nitrobenzoate
  参考文献：
  名称：

  An Organocascade Kinetic Resolution

  摘要：

  Products of a novel iminium-catalyzed oxa-Michael addition undergo a kinetic resolution by a subsequent enamine-catalyzed intermolecular reaction. This is a rare example of kinetic resolution by enamine catalysis and the first organocascade kinetic resolution. This resolution produces enantioenriched 2,6-cis-tetrahydropyrans and, notably, cascade products with absolute and relative configurations normally not observed using this diphenyl prolinol silyl ether. This resolution thus provides new insight into asymmetric induction in reactions employing this catalyst.

  DOI：

  10.1021/ol2027587
• 作为产物：
  描述：

  、 丁烯-2-醛 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以79%的产率得到(E)-methyl 9-hydroxy-15-oxopentadec-13-enoate
  参考文献：
  名称：

  An Organocascade Kinetic Resolution

  摘要：

  Products of a novel iminium-catalyzed oxa-Michael addition undergo a kinetic resolution by a subsequent enamine-catalyzed intermolecular reaction. This is a rare example of kinetic resolution by enamine catalysis and the first organocascade kinetic resolution. This resolution produces enantioenriched 2,6-cis-tetrahydropyrans and, notably, cascade products with absolute and relative configurations normally not observed using this diphenyl prolinol silyl ether. This resolution thus provides new insight into asymmetric induction in reactions employing this catalyst.

  DOI：

  10.1021/ol2027587