(2R)-2-(1,3-dioxoisoindol-2-yl)-3-(4-methoxyphenyl)propanoic acid | 1242459-49-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R)-2-(1,3-dioxoisoindol-2-yl)-3-(4-methoxyphenyl)propanoic acid
• CAS: 1242459-49-9
• 化学式: C₁₈H₁₅NO₅
• 分子量: 325.321
• InChiKey: SLJWULOHSPROGQ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 (2R)-2-(1,3-dioxoisoindol-2-yl)-3-(4-methoxyphenyl)propanoic acid 在 正丁基锂 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以45%的产率得到2-[3-(4-Methoxyphenyl)-1,1-bis(trimethylsilyloxy)prop-1-en-2-yl]isoindole-1,3-dione
  参考文献：
  名称：

  Catalytic Asymmetric Protonation of α-Amino Acid-Derived Ketene Disilyl Acetals Using P-Spiro Diaminodioxaphosphonium Barfates as Chiral Proton

  摘要：

  Chiral diaminodioxaphosphonium salts have been developed and their unique abilities as a chiral proton have been revealed through the establishment of a highly enantioselective protonation of alpha-amino acid-derived ketene disilyl acetals.

  DOI：

  10.1021/ja105945z
• 作为产物：
  描述：

  2-[3-(4-Methoxyphenyl)-1,1-bis(trimethylsilyloxy)prop-1-en-2-yl]isoindole-1,3-dione 在 2,6-二叔丁基吡啶 、 2,6-二甲基苯酚 、 C₃₂H₁₂BF₂₄^(1-)*C₄₄H₃₀N₂O₂P⁽¹⁺⁾ 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以100%的产率得到(2R)-2-(1,3-dioxoisoindol-2-yl)-3-(4-methoxyphenyl)propanoic acid
  参考文献：
  名称：

  Catalytic Asymmetric Protonation of α-Amino Acid-Derived Ketene Disilyl Acetals Using P-Spiro Diaminodioxaphosphonium Barfates as Chiral Proton

  摘要：

  Chiral diaminodioxaphosphonium salts have been developed and their unique abilities as a chiral proton have been revealed through the establishment of a highly enantioselective protonation of alpha-amino acid-derived ketene disilyl acetals.

  DOI：

  10.1021/ja105945z

文献信息

• 10.1002/anie.202405062
  作者：Yuan, Chen-Hui、Wang, Xiao-Xia、Huang, Keyun、Jiao, Lei

  DOI：10.1002/anie.202405062

  日期：——

  AbstractPalladium‐catalyzed enantioselective C(sp3)−H functionalization reactions has attracted considerable attention due to its ability for the synthesis of enantiomerically enriched molecules and stimulation of novel retrosynthetic disconnections. Understanding the reaction mechanism, especially the stereochemical process of the reaction, is crucial for the rational design of more efficient catalytic systems. Previously, we developed a Pd(II)/sulfoxide‐2‐hydroxypridine (SOHP) catalytic system for asymmetric C(sp3)−H functionalization reactions. In this study, we focused on unraveling the chemistry of chiral palladacycles involved in the Pd(II)‐catalyzed enantioselective C(sp3)−H functionalization. We have isolated key palladacycle intermediates involved in the enantioselective β‐C(sp3)−H arylation of carboxylic acids catalyzed by the Pd(II)/SOHP system. These palladacycles, exhibiting ligand‐induced chirality, provided a significant opportunity to investigate the stereochemical process and the ligand effect in this asymmetric C−H functionalization. Our investigation provided direct evidence for the C−H palladation step as the enantioselectivity‐determining step, which forms diastereomeric palladacycles that exhibited preservation of chirality in the functionalization step. DFT calculations provided insights into the chiral induction in palladacycle formation. This work highlights the value of chiral palladacycle chemistry in offering mechanistic insights into the Pd(II)‐catalyzed asymmetric C(sp3)−H functionalization reactions.
• Catalytic Asymmetric Protonation of α-Amino Acid-Derived Ketene Disilyl Acetals Using <i>P</i>-Spiro Diaminodioxaphosphonium Barfates as Chiral Proton
  作者：Daisuke Uraguchi、Natsuko Kinoshita、Takashi Ooi

  DOI：10.1021/ja105945z

  日期：2010.9.8

  Chiral diaminodioxaphosphonium salts have been developed and their unique abilities as a chiral proton have been revealed through the establishment of a highly enantioselective protonation of alpha-amino acid-derived ketene disilyl acetals.