(2S,3S)-dimethyl 2-hydroxy-3-((E)-2-(7-methoxynaphthalen-2-yl)vinyl)-2-(trifluoromethyl)succinate | 1594882-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,3S)-dimethyl 2-hydroxy-3-((E)-2-(7-methoxynaphthalen-2-yl)vinyl)-2-(trifluoromethyl)succinate
• 英文别名: dimethyl (2S,3S)-2-hydroxy-3-[(E)-2-(7-methoxynaphthalen-2-yl)ethenyl]-2-(trifluoromethyl)butanedioate
• CAS: 1594882-38-8
• 化学式: C₂₀H₁₉F₃O₆
• 分子量: 412.362
• InChiKey: BUCGBXGFSHBONB-RCCFSGOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  甲醇 、 三氟丙酮酸甲酯 、 在 (5aR,10bS)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride 、 dipotassium hydrogenphosphate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 21.0h， 以97%的产率得到
  参考文献：
  名称：

  Catalytic Asymmetric α-Aldol Reaction of Vinylogous N-Heterocyclic Carbene Enolates: Formation of Quaternary and Labile Tertiary Stereocenters

  摘要：

  Simple N-heterocyclic carbene (NHC)-enolates are widely studied versatile species. However, their vinylogous siblings (i.e., vinylogous NHC-enolates) have been much less studied. Here we disclose the first catalytic asymmetric a-aldol reaction of vinylogous NHC-enolates. With trifluoropyruvate as the carbon electrophile, the efficient C C bond formation process displays not only complete alpha-regioselectivity but also excellent stereocontrol over the two newly established challenging stereocenters (one quaternary and the other labile tertiary), furnishing a range of highly enantioenriched beta,gamma-unsaturated alpha-fluoroalkylated esters.

  DOI：

  10.1021/ol500830a

文献信息

• Catalytic Asymmetric α-Aldol Reaction of Vinylogous <i>N</i>-Heterocyclic Carbene Enolates: Formation of Quaternary and Labile Tertiary Stereocenters
  作者：Xiuqin Dong、Jianwei Sun

  DOI：10.1021/ol500830a

  日期：2014.5.2

  Simple N-heterocyclic carbene (NHC)-enolates are widely studied versatile species. However, their vinylogous siblings (i.e., vinylogous NHC-enolates) have been much less studied. Here we disclose the first catalytic asymmetric a-aldol reaction of vinylogous NHC-enolates. With trifluoropyruvate as the carbon electrophile, the efficient C C bond formation process displays not only complete alpha-regioselectivity but also excellent stereocontrol over the two newly established challenging stereocenters (one quaternary and the other labile tertiary), furnishing a range of highly enantioenriched beta,gamma-unsaturated alpha-fluoroalkylated esters.