| 1427072-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1427072-38-5
• 化学式: C₁₆H₁₉FO₈
• 分子量: 358.32
• InChiKey: MTJQGSYAXWTHJA-YETHDTDJSA-N

反应信息

• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 草酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 、
  参考文献：
  名称：

  A new approach to the synthesis of (Z)-2-fluoro-2-alkenals via Wittig-type carbonyl condensation reactions of 2-(fluoromethyl)-4,4,6-trimethyl-1,3-oxazine phosphonium bromide

  摘要：

  We report here the transformation of aldehydes to their (Z)-alpha-fluoro-alpha,beta-unsaturated aldehyde homologs by condensation with the phosphonium salt of the Meyer's oxazine obtained from bromofluoroacetonitrile. After methylation with trimethyloxonium tetrafluoroborate the quaternized oxazine is cleanly reduced to mostly Z 2-fluoro-2-alkenals by sodium borohydride at room temperature. This methodology is compatible with usual protecting groups and affords an efficient access to functionalized mostly Z 2-fluoro-2-alkenals derived from natural products and their corresponding (Z)-2-fluoro-2-alkenols. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.017