(2S,3S,4S)-2-(tert-butyldiphenylsiloxy)-4-methyl-5-hexen-3-ol | 1245571-54-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3S,4S)-2-(tert-butyldiphenylsiloxy)-4-methyl-5-hexen-3-ol
• 英文别名: (2S,3S,4S)-2-[tert-butyl(diphenyl)silyl]oxy-4-methylhex-5-en-3-ol
• CAS: 1245571-54-3
• 化学式: C₂₃H₃₂O₂Si
• 分子量: 368.591
• InChiKey: JXKJWUAFUFPQAG-IPJJNNNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-2-(tert-butyldiphenylsiloxy)-4-methyl-5-hexen-3-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S,4S)-4-methylhex-5-ene-2,3-diol
  参考文献：
  名称：

  Stereocontrolled palladium-catalysed umpolung allylation of aldehydes with allyl acetates

  摘要：

  In the present work the stereocontrolled palladium-catalysed umpolung allylation of aldehydes is described. Allyl acetates are in situ transformed into the corresponding allyl boronates, which directly react with aldehydes. The question of stereocontrol is raised by employing (a) chiral boronating agents (reagent control) and by (b) utilising chiral aldehydes (substrate control). These studies reveal that the approach based on substrate control is superior to the former one with respect to yields and stereo-selectivity. Remarkably, this umpolung protocol often yields the 4,5-syn products in high selectivity, which is unprecedented for direct crotylations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.133
• 作为产物：
  描述：

  (S)-2-(叔丁基二苯基硅氧基)丙醛 、 反式-巴豆基硼酸频哪醇酯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 联硼酸频那醇酯 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 生成 (2S,3R,4R)-2-(tert-butyldiphenylsiloxy)-4-methyl-5-hexen-3-ol 、 (2S,3S,4S)-2-(tert-butyldiphenylsiloxy)-4-methyl-5-hexen-3-ol
  参考文献：
  名称：

  Stereocontrolled palladium-catalysed umpolung allylation of aldehydes with allyl acetates

  摘要：

  In the present work the stereocontrolled palladium-catalysed umpolung allylation of aldehydes is described. Allyl acetates are in situ transformed into the corresponding allyl boronates, which directly react with aldehydes. The question of stereocontrol is raised by employing (a) chiral boronating agents (reagent control) and by (b) utilising chiral aldehydes (substrate control). These studies reveal that the approach based on substrate control is superior to the former one with respect to yields and stereo-selectivity. Remarkably, this umpolung protocol often yields the 4,5-syn products in high selectivity, which is unprecedented for direct crotylations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.133

文献信息

• Stereocontrolled palladium-catalysed umpolung allylation of aldehydes with allyl acetates
  作者：Monika Vogt、Sascha Ceylan、Andreas Kirschning

  DOI：10.1016/j.tet.2010.04.133

  日期：2010.8

  In the present work the stereocontrolled palladium-catalysed umpolung allylation of aldehydes is described. Allyl acetates are in situ transformed into the corresponding allyl boronates, which directly react with aldehydes. The question of stereocontrol is raised by employing (a) chiral boronating agents (reagent control) and by (b) utilising chiral aldehydes (substrate control). These studies reveal that the approach based on substrate control is superior to the former one with respect to yields and stereo-selectivity. Remarkably, this umpolung protocol often yields the 4,5-syn products in high selectivity, which is unprecedented for direct crotylations. (C) 2010 Elsevier Ltd. All rights reserved.