tert-butyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate | 83945-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate
• CAS: 83945-71-5
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: JYUCJWFNNCSFPX-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙烯酸叔丁酯 以 乙醚 为溶剂， 反应 20.0h， 生成 t-butyl(2R,3S)-(+)-2-methyl-3-hydroxy-3-phenylpropionate 、 tert-butyl 3-hydroxy-2-methyl-3-phenylpropionate 、 tert-butyl(2R,3R)-3-hydroxy-2-methyl-3-phenylpropionate 、 tert-butyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate
  参考文献：
  名称：

  (Diisopinocampheyl)borane-Mediated Reductive Aldol Reactions of Acrylate Esters: Enantioselective Synthesis of Anti-Aldols

  摘要：

  The (diisopinocampheyl)borane promoted reductive aldol reaction of acrylate esters 4 is described. Isomerization of the kinetically formed Z(O)-enolborinate 5Z to the thermodynamic E(O)-enolborinate 5E via 1,3-boratropic shifts, followed by treatment with representative achiral aldehydes, leads to anti-alpha-methyl-beta-hydroxy esters 9 or 10 with excellent diastereo- (up to >= 20:1 dr) and enantioselectivity (up to 87% ee). The results of double asymmetric reactions of 5E with several chiral aldehydes are also presented.

  DOI：

  10.1021/ol401679g

文献信息

• High Performance of Rh(Phebox) Catalysts in Asymmetric Reductive Aldol Reaction:  High Anti-Selectivity
  作者：Hisao Nishiyama、Takushi Shiomi、Yasunori Tsuchiya、Isamu Matsuda

  DOI：10.1021/ja050698m

  日期：2005.5.1

  Chiral rhodium(bisoxazolinylphenyl) complexes (1 mol %) efficiently catalyze the asymmetric reductive aldol reaction of aldehydes and alpha,beta-unsaturated esters at 50 degrees C for ca. 0.5-1.0 h with several hydrosilanes to give the corresponding beta-hydroxypropionates with extremely high anti-selectivity (up to 98%) and enantioselectivity (up to 96% ee). The stereochemical outcome is likely due

  手性铑(双恶唑啉基苯基) 配合物 (1 mol %) 有效地催化醛和 α，β-不饱和酯在 50 摄氏度的不对称还原醛醇反应约。使用几种氢硅烷反应 0.5-1.0 小时，得到具有极高抗选择性（高达 98%）和对映选择性（高达 96% ee）的相应 β-羟基丙酸酯。立体化学结果可能是由于涉及铑-(E)-烯醇化物的椅子状循环过渡态。
• Efficient Preparation of New Rhodium- and Iridium-[Bis(oxazolinyl)-3,5-dimethylphenyl] Complexes by CH Bond Activation: Applications in Asymmetric Synthesis
  作者：Jun-ichi Ito、Takushi Shiomi、Hisao Nishiyama

  DOI：10.1002/adsc.200606049

  日期：2006.7

  -iridium complexes were synthesized in high yields by an efficient CH bond activation method with 4,6-dimethyl-1,3-bis(oxazolinyl)benzene derivatives. The catalytic activity of the complexes was examined for the asymmetric conjugate reduction of (E)-ethyl 3-phenylbut-2-enoate and the asymmetric reductive aldol reaction of tert-butyl acrylate and benzaldehyde. It was found that the rhodium complex of 3

  通过有效的CH键活化方法，用4,6-二甲基-1,3-双（恶唑啉基）苯衍生物以高收率合成了双（恶唑啉基）-3,5-二甲基苯基铑和-铱配合物。检测了配合物的催化活性，以观察到（E）-3-苯基丁-2-烯酸酯的不对称共轭还原以及丙烯酸叔丁酯与苯甲醛的不对称还原醛醇缩合反应。发现3，5-dmPhebox的铑配合物显示出较高的催化活性，而相应的铱配合物被证明活性较低。
• 4-Substituted-Phenyl(bisoxazoline)-Rhodium Complexes: Efficiency in the Catalytic Asymmetric Reductive Aldol Reaction
  作者：Takushi Shiomi、Jun-ichi Ito、Yoshihiko Yamamoto、Hisao Nishiyama

  DOI：10.1002/ejoc.200600722

  日期：2006.12

  substituents on the phenyl ring of the phenyl(bisoxazoline) ligand skeleton of rhodium catalysts was examined in the asymmetric reductive aldol reactions of acrylates and aldehydes. The electron-withdrawing NO2 group of Rh(4-NO2-Phebox-R)(OAc)2 showed an increase in the enantioselectivity of the products in the reductive reaction of methyl acrylate but not in the reactions of tert-butyl- and trimethylsilyl acrylates

  在丙烯酸​​酯和醛的不对称还原醛醇反应中检查了取代基对铑催化剂的苯基（双恶唑啉）配体骨架的苯环的电子效应。Rh(4-NO2-Phebox-R)(OAc)2 的吸电子 NO2 基团在丙烯酸甲酯的还原反应中显示出产物的对映选择性增加，但在丙烯酸叔丁酯和三甲基甲硅烷基酯的反应中没有增加. 相应模型铑-Phebox 配合物的理论计算表明远程吸电子取代基略微缩短了 Rh-Cphebox 键。此外，在 X 射线分析的基础上比较了 Rh(4-NO2-Phebox-iPr)(OAc)2 和相应的 Rh(4-H-Phebox-iPr)(OAc)2 的 Rh-C 键。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Versatile chiral reagent for the highly enantioselective synthesis of either anti or syn ester aldols
  作者：E. J. Corey、Sung Soo Kim

  DOI：10.1021/ja00168a062

  日期：1990.6