(R)-(+)-diethyl 2-(1,1'-binaphthyl)phosphonate | 1372202-86-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-(+)-diethyl 2-(1,1'-binaphthyl)phosphonate
• 英文别名: diethyl 2-(1,1'-binaphthyl)phosphonate；Diethyl 1,1'-binaphthyl-2-ylphosphonate；2-diethoxyphosphoryl-1-naphthalen-1-ylnaphthalene
• CAS: 1372202-86-2
• 化学式: C₂₄H₂₃O₃P
• 分子量: 390.419
• InChiKey: CRWXVKGFVATNBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-diethyl 2-(1,1'-binaphthyl)phosphonate 在 palladium diacetate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 生成 (R)-2'-(diphenylphosphoryl)-1,1'-binaphthyl-2-yl acetate
  参考文献：
  名称：

  P(O)R2 导向的 Pd 催化的联芳基衍生物 CH 官能化合成手性磷配体。

  摘要：

  手性磷配体已广泛用于过渡金属催化的不对称反应。在此，我们报告了一种使用 P(O)R2 导向的 Pd 催化 CH 活化合成含磷部分的手性联芳基化合物的新方法；功能化产物具有良好的对映选择性。

  DOI：

  10.3762/bjoc.10.215
• 作为产物：
  描述：

  (R)-2-(diethoxyphosphoryl)-2'-((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl 生成 (R)-(+)-diethyl 2-(1,1'-binaphthyl)phosphonate
  参考文献：
  名称：

  KURZ, LILIA;LEE, GARY;MORGANS, DAVID (JR);WALDYKE, MICHAEL JOE;WARD, TIMO+, TETRAHEDRON LETT., 31,(1990) N4, C. 6321-6324

  摘要：

  DOI：

文献信息

• Efficient Chiral Monophosphorus Ligands for Asymmetric Suzuki–Miyaura Coupling Reactions
  作者：Wenjun Tang、Nitinchandra D. Patel、Guangqing Xu、Xiaobing Xu、Jolaine Savoie、Shengli Ma、Ming-Hong Hao、Santosh Keshipeddy、Andrew G. Capacci、Xudong Wei、Yongda Zhang、Joe J. Gao、Wenjie Li、Sonia Rodriguez、Bruce Z. Lu、Nathan K. Yee、Chris H. Senanayake

  DOI：10.1021/ol300659d

  日期：2012.5.4

  A series of novel P-chiral monophosphorus ligands exhibit efficiency in asymmetric Suzuki–Miyaura coupling reactions, enabling the construction of an array of chiral biaryl products in high yields and excellent enantioselectivities (up to 96% ee) under mild conditions. The carbonyl-benzooxazolidinone moiety in these chiral biaryl products allows facile derivatization for further synthetic applications

  一系列新颖的P-手性单磷配体在不对称Suzuki-Miyaura偶联反应中表现出效率，使得在温和条件下能够以高收率和出色的对映选择性（高达96％ee）构建一系列手性联芳基产品。这些手性联芳基产物中的羰基-苯并恶唑烷酮部分允许容易地衍生化，以用于进一步的合成应用。一项计算研究表明，两个偶联伙伴之间的π-π相互作用可以增强偶联反应的对映选择性。
• Highly Efficient Synthesis of a Class of Novel Chiral-Bridged Atropisomeric Monophosphine Ligands via Simple Desymmetrization and Their Applications in Asymmetric Suzuki–Miyaura Coupling Reaction
  作者：Shouliang Wang、Jinjin Li、Tingting Miao、Wenhao Wu、Qing Li、Yue Zhuang、Zhongyuan Zhou、Liqin Qiu

  DOI：10.1021/ol300721p

  日期：2012.4.20

  A series of novel chiral-bridged atropisomeric monophosphine ligands were synthesized via convenient and simple pathways. The prepared ligands, especially for ligand 7d, were found to be highly effective in the Pd-catalyzed Suzuki–Miyaura coupling reaction. The steric hindrance and electronic effect of substrates on the reactivity and enantioselectivity were explored preliminarily.

  通过方便和简单的途径合成了一系列新颖的手性桥联的阻转异构单膦配体。发现制备的配体，特别是配体7d，在Pd催化的Suzuki-Miyaura偶联反应中非常有效。初步探讨了底物的空间位阻和电子效应对反应性和对映选择性的影响。
• Highly Diastereoselective Synthesis of Atropisomeric Bridged P,N‐Ligands and Their Applications in Asymmetric Suzuki–Miyaura Coupling Reaction
  作者：Wenhao Wu、Shouliang Wang、Yougui Zhou、Yuwei He、Yue Zhuang、Lanning Li、Pin Wan、Longshu Wang、Zhongyuan Zhou、Liqin Qiu

  DOI：10.1002/adsc.201200095

  日期：2012.9.17

  atropisomeric bridged P,N‐ligands were prepared using a highly efficient central‐to‐axial transfer strategy as the protocol. The new chiral ligands were successfully applied in the palladium‐catalyzed asymmetric Suzuki–Miyaura coupling reaction, Up to 98% yield and 82% ee were obtained in the enantioselective synthesis of axially chiral biarylphosphonates.

  使用高效的中心到轴向转移策略作为方案，制备了三种新颖的阻转异构体桥接的P，N-配体。新的手性配体已成功地应用于钯催化的不对称Suzuki-Miyaura偶联反应中，轴向手性联芳基膦酸酯的对映选择性合成获得了高达98％的收率和82％的ee。
• Palladium(<scp>ii</scp>) complexes with planar chiral ferrocenyl phosphane–(benz)imidazol-2-ylidene ligands
  作者：Pauline Loxq、Nathalie Debono、Süleyman Gülcemal、Jean-Claude Daran、Eric Manoury、Rinaldo Poli、Bekir Çetinkaya、Agnès Labande

  DOI：10.1039/c3nj00863k

  日期：——

  We describe here the first examples of planar chiral ferrocenyl phosphane–benzimidazol-2-ylidene ligands and their coordination chemistry with palladium(II). All ligand precursors, namely enantiopure ferrocenyl phosphane–(benz)imidazolium salts, and all enantiopure palladium complexes have been fully characterised by 1H, 31P and 13C NMR, mass spectrometry and X-ray diffraction methods for seven examples. The potential of these very bulky bidentate ligands in catalysis was evaluated and compared to their imidazol-2-ylidene analogues. The influence of sterics was shown to be non-negligible as the bulkiest ligand gave the lowest activities in the asymmetric Suzuki–Miyaura reaction.

  我们在此介绍了平面手性二茂铁磷烷苯并咪唑-2-亚基配体及其与钯（II）的配位化学反应。通过 1H、31P 和 13C NMR、质谱和 X 射线衍射方法，对所有配体前体（即对映纯二茂铁磷烷苯并咪唑盐）和所有对映纯钯配合物进行了全面表征，共七个实例。对这些非常笨重的双齿配体的催化潜力进行了评估，并与它们的咪唑-2-亚基类似物进行了比较。结果表明，在不对称铃木-米亚乌拉反应中，最粗大配体的活性最低，因此立体结构的影响不可忽视。
• Synthesis of Chiral-Bridged Atropisomeric Monophosphine Ligands with Tunable Dihedral Angles and their Applications in Asymmetric Suzuki-Miyaura Coupling Reactions
  作者：Wang Xia、Yongsu Li、Zihong Zhou、Huixuan Chen、Hao Liang、Sifan Yu、Xuefeng He、Yaqi Zhang、Jiyan Pang、Zhongyuan Zhou、Liqin Qiu

  DOI：10.1002/adsc.201700020

  日期：2017.5.17

  construction of diastereomeric biaryl monophosphines by means of the substrate-directed asymmetric annulation reactions. A series of new chiral-bridged atropisomeric biphenyl monophosphine ligands with tunable dihedral angles was accordingly synthesized successfully without a resolution step being needed. Using these ligands, different kinds of axially chiral 1,1′-biaryl-2-phosphonates including the first

  在非对映体联芳基单膦化合物的构建中，首先通过底物定向的不对称环化反应实现了精确的手性识别。因此，成功地合成了具有可调二面角的一系列新的手性桥联的阻转异构联苯单膦配体，而无需拆分步骤。使用这些配体，通过钯催化的不对称Suzuki偶联反应，可以制备42-97％的产率的轴向手性1,1'-联芳基-2-膦酸酯，包括首次报道的喹啉基联芳基膦酸酯，最高可达96％ee。