(1S,2R)-1-(6-bromopyridin-2-yl)but-3-ene-1,2-diol | 1208092-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (1S,2R)-1-(6-bromopyridin-2-yl)but-3-ene-1,2-diol
• 英文别名: (1S,2R)-1-(6-Bromo-2-pyridinyl)-3-butene-1,2-diol
• CAS: 1208092-42-5
• 化学式: C₉H₁₀BrNO₂
• 分子量: 244.088
• InChiKey: WNAICLDGQYFHSY-APPZFPTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-溴吡啶-2-甲醛 、 acrolein gem-dibenzoate 在 potassium phosphate 、 (R)-SEGPHOS-I 、 异丙醇 、 甲醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 66.0h， 生成 (1S,2R)-1-(6-bromopyridin-2-yl)but-3-ene-1,2-diol 、
  参考文献：
  名称：

  Diastereo- and Enantioselective anti-Alkoxyallylation Employing Allylic gem-Dicarboxylates as Allyl Donors via Iridium-Catalyzed Transfer Hydrogenation

  摘要：

  Enantioselective transfer hydrogenation of gem-dibenzoate le in the presence of aromatic. alpha,beta-unsaturated, or aliphatic aldehydes 2a-i mediated by isopropyl alcohol and employing a cyclometalated iridium C,O-benzoate derived from allyl acetate, 4-cyano-3-nitrobenzoic acid, and (R)-SEGPHOS delivers products Of alkoxyallylation 3a-i, 4a, 4e, 4f, and 4i in good isolated yields (62-82%) with good to excellent diastereoselectivities (7:1 to 18:1 dr) and exceptional enantioselectivities (90-99% ee). This protocol provides an alternative to the Use of premetalated nucleophiles in carbonyl alkoxyallylation.

  DOI：

  10.1021/ja9097675

文献信息

• Diastereo- and Enantioselective <i>anti</i>-Alkoxyallylation Employing Allylic <i>gem</i>-Dicarboxylates as Allyl Donors via Iridium-Catalyzed Transfer Hydrogenation
  作者：Soo Bong Han、Hoon Han、Michael J. Krische

  DOI：10.1021/ja9097675

  日期：2010.2.17

  Enantioselective transfer hydrogenation of gem-dibenzoate le in the presence of aromatic. alpha,beta-unsaturated, or aliphatic aldehydes 2a-i mediated by isopropyl alcohol and employing a cyclometalated iridium C,O-benzoate derived from allyl acetate, 4-cyano-3-nitrobenzoic acid, and (R)-SEGPHOS delivers products Of alkoxyallylation 3a-i, 4a, 4e, 4f, and 4i in good isolated yields (62-82%) with good to excellent diastereoselectivities (7:1 to 18:1 dr) and exceptional enantioselectivities (90-99% ee). This protocol provides an alternative to the Use of premetalated nucleophiles in carbonyl alkoxyallylation.