(2S,3S)-2-vinyl-3-(tert-butyldimethylsilyloxy)-3-phenylpropanoic acid | 1190930-26-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S,3S)-2-vinyl-3-(tert-butyldimethylsilyloxy)-3-phenylpropanoic acid
• CAS: 1190930-26-7
• 化学式: C₁₇H₂₆O₃Si
• 分子量: 306.477
• InChiKey: VYYSVIWBJHCDOC-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (4S,2'S,3'S)-N(3)-[2'-vinyl-3'-(tert-butyldimethylsilyloxy)-30-phenylpropanoyl]-4-isopropyl-5,5-dimethyl-oxazolidin-2-one 在 水 、 双氧水 、 lithium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以92%的产率得到(2S,3S)-2-vinyl-3-(tert-butyldimethylsilyloxy)-3-phenylpropanoic acid
  参考文献：
  名称：

  The dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat: asymmetric synthesis of α-vinyl-β-hydroxycarboxylic acid derivatives and conversion to α-ethylidene-β-hydroxyesters (β-substituted Baylis–Hillman products)

  摘要：

  The synthesis of alpha-vinyl-beta-hydroxyesters and alpha-ethlylidene-beta-hydroxyesters (beta-substituted Baylis-Hillman products) Via the dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat is described. High levels of syn-diastereoselectivity (up to >98% de) are observed for the dienolate aldol reaction with boron enolates, generated either directly with Bu2BOTf or by transmetalation of the potassium enolate with B-bromocatecholborane. Cleavage of the resultant syn-aldol products from the auxiliary gives alpha-vinyl-beta-hydroxyesters in >98% de and >98% ee. Subsequent isomerisation of the double bond into conjugation provides alpha-ethylidene-beta-hydroxyesters (beta-substituted Baylis-Hillman products) in high diastereo- and enantiopurity (>= 91:9 |(E):(Z)| and >98% ee). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.004