(3R,4S,E)-6-(dimethyl(phenyl)silyl)-4-methyl-1-phenylhex-5-en-3-ol | 1428744-64-2

• 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: (3R,4S,E)-6-(dimethyl(phenyl)silyl)-4-methyl-1-phenylhex-5-en-3-ol
• 英文别名: (E,3R,4S)-6-[dimethyl(phenyl)silyl]-4-methyl-1-phenylhex-5-en-3-ol
• CAS: 1428744-64-2
• 化学式: C₂₁H₂₈OSi
• 分子量: 324.538
• InChiKey: KOGFQULLUKBZMK-KGOBOVKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 diisopinocampheylborane 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 (3R,4S,E)-6-(dimethyl(phenyl)silyl)-4-methyl-1-phenylhex-5-en-3-ol
  参考文献：
  名称：

  Enantiodivergent hydroboration reactions of a racemic allenylsilane with diisopinocampheylborane and Curtin–Hammett controlled double asymmetric crotylboration reactions of (S)-E-α-phenyldimethylsilyl(ddiisopinocampheyl)-crotylborane

  摘要：

  The enantiodivergent hydroboration reactions of racemic allenylsilane (+/-)-4 with ((d)Ipc)(2)BH and subsequent crotylboration of achiral aldehydes with the product crotylborane (S)-E-5 at -78 degrees C provide (E)-delta-silyl-anti-homoallylic alcohols 6 in 71-89% yield and with 93-96% ee. Intriguingly, mismatched double asymmetric crotylboration reactions of enantioenriched chiral aldehydes 20 with (S)-E-5 proceed under Curtin-Hammett control to give anti-beta-hydroxylcrotylsilanes 24 as the only products. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.098

文献信息

• Reprint of: Enantiodivergent hydroboration reactions of a racemic allenylsilane with diisopinocampheylborane and Curtin–Hammett controlled double asymmetric crotylboration reactions of (S)-E-α-phenyldimethylsilyl(ddiisopinocampheyl)-crotylborane
  作者：Ming Chen、William R. Roush

  DOI：10.1016/j.tet.2013.06.053

  日期：2013.9

  The enantiodivergent hydroboration reactions of racemic allenylsilane (+/-)-4 with ((d)Ipc)(2)BH and subsequent crotylboration of achiral aldehydes with the product crotylborane (S)-E-5 at -78 degrees C provide (E)-delta-silyl-anti-homoallylic alcohols 6 in 71-89% yield and with 93-96% ee. Intriguingly, mismatched double asymmetric crotylboration reactions of enantioenriched chiral aldehydes 20 with (S)-E-5 proceed under Curtin-Hammett control to give anti-beta-hydroxylcrotylsilanes 24 as the only products. (C) 2013 Elsevier Ltd. All rights reserved.
• Enantioselective Synthesis of (<i>E</i>)-δ-Silyl-<i>anti</i>-homoallylic Alcohols via an Enantiodivergent Hydroboration-Crotylboration Reaction of a Racemic Allenylsilane
  作者：Ming Chen、William R. Roush

  DOI：10.1021/ol4004405

  日期：2013.4.5

  The enantioselective hydroboration of racemic allenylsilane (+/-)-4 with ((d)Ipc)(2)BH proceeds via enantiodivergent pathways to give vinylborane 11 and crotylborane intermediate (S)-E-5. Subsequent crotylboration of aldehyde substrates with (S)-E-5 at -78 degrees C provides (E)-delta-silyl-anti-homoallylic alcohols in 71-89% yield and with 93-96% ee.
• Enantiodivergent hydroboration reactions of a racemic allenylsilane with diisopinocampheylborane and Curtin–Hammett controlled double asymmetric crotylboration reactions of (S)-E-α-phenyldimethylsilyl(ddiisopinocampheyl)-crotylborane
  作者：Ming Chen、William R. Roush

  DOI：10.1016/j.tet.2013.04.098

  日期：2013.7

  The enantiodivergent hydroboration reactions of racemic allenylsilane (+/-)-4 with ((d)Ipc)(2)BH and subsequent crotylboration of achiral aldehydes with the product crotylborane (S)-E-5 at -78 degrees C provide (E)-delta-silyl-anti-homoallylic alcohols 6 in 71-89% yield and with 93-96% ee. Intriguingly, mismatched double asymmetric crotylboration reactions of enantioenriched chiral aldehydes 20 with (S)-E-5 proceed under Curtin-Hammett control to give anti-beta-hydroxylcrotylsilanes 24 as the only products. (C) 2013 Elsevier Ltd. All rights reserved.