(S)-3,3'-dibenzhydryl-2,2'-dihydroxyl-1,1'-binaphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-3,3'-dibenzhydryl-2,2'-dihydroxyl-1,1'-binaphthalene
• 英文别名: (S)-3,3'-dibenzhydryl-[1,1'-binaphthalene]-2,2'-diol；3-benzhydryl-1-(3-benzhydryl-2-hydroxynaphthalen-1-yl)naphthalen-2-ol
• 化学式: C₄₆H₃₄O₂
• 分子量: 618.775
• InChiKey: DUJIWKYJZJIBEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  48
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3,3'-dibenzhydryl-2,2'-dihydroxyl-1,1'-binaphthalene 在 三乙胺 、 三氯化磷 、 水 作用下， 以 甲苯 为溶剂， 以33 %的产率得到(11bS)-2,6-dibenzhydryldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide
  参考文献：
  名称：

  三氟甲硫醇内炔的配体控制区域发散烷氧基羰基化

  摘要：

  控制不对称内炔烷氧基羰基化的区域选择性具有挑战性。在此，实现了内部三氟甲基硫醇炔烃的钯催化配体控制的区域发散烷氧基羰基化。由相同的三氟甲硫醇炔获得了一系列α-或β-SCF 3丙烯酸酯，具有中等到高产率和区域选择性。

  DOI：

  10.1021/acs.orglett.4c01113
• 作为产物：
  描述：

  (R)-(+)-2,2’-双(甲氧基甲氧基)-1,1’-联萘 在 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 (S)-3,3'-dibenzhydryl-2,2'-dihydroxyl-1,1'-binaphthalene
  参考文献：
  名称：

  Asymmetric Intramolecular Hydroamination of Allenes using Mononuclear Gold Catalysts

  摘要：

  The intramolecular gold-catalyzed asymmetric hydroamination of allenes was studied by screening a series of mononuclear gold(I) and -(III) complexes in combination with silver salts. Among the various chiral monophosphine and diaminocarbene ligands tried, the best catalysts arose from mononuclear gold(I) complexes synthesized from BINOL-based phosphoramidite ligands. The latest were improved by addition of bulky substituents at specific positions of the BINOL scaffold. The resulting gold(I) complexes were combined with selected silver salts to afford efficient catalysts for intramolecular hydroamination of allenes at room temperature or below, with good conversions and enantioselectivities.

  DOI：

  10.1021/om4009058

文献信息

• Synthesis and application of bulky phosphoramidites: highly effective monophosphorus ligands for asymmetric hydrosilylation of styrenes
  作者：Feng Zhang、Qing-Hua Fan

  DOI：10.1039/b909334f

  日期：——

  A series of bulky monodentate phosphoramidite ligands were synthesized from chiral 3,3′-diaryl substituted BINOL derivatives and achiral or dendritic amines in good yields. Asymmetric hydrosilylation of styrenes with trichlorosilane in the presence of palladium complexes of these bulky ligands gave chiral silanes in high yields with excellent activity and productivity. Oxidation of these chiral silanes

  从手性3,3'-二芳基取代的BINOL衍生物和非手性或树枝状胺合成了一系列庞大的单齿亚磷酰胺配体，收率很高。苯乙烯与硅的不对称氢化硅烷化三氯硅烷在这些庞大的配体的钯配合物存在下，以高产率得到具有优异活性和生产率的手性硅烷。这些手性硅烷的氧化过氧化氢 得到了最高96％ee的相应手性仲醇。
• Synthesis and Application of 3,3′-Diarylmethyl BINOLs
  作者：Qing-Hua Fan、Yi-Li Zhang、Feng Zhang、Wei-Jun Tang、Qing-Lai Wu

  DOI：10.1055/s-2006-932475

  日期：——

  A new class of 3,3′-diarylmethyl BINOL derivatives were synthesized and applied to the catalytic asymmetric addition of diethylzinc to aldehydes. These chiral diol auxiliaries could be used as catalysts without the addition of Ti(i-PrO)4 and showed unprecedented catalytic activities and enantioselectivities (up to 94% ee, 5 mol% catalyst loading).

  合成了一类新的3,3′-二芳基甲基BINOL衍生物，并将其应用于二乙基锌对醛的催化不对称加成反应。这些手性二醇辅助剂可以作为催化剂使用，而无需添加Ti(i-PrO)4，并表现出前所未有的催化活性和对映选择性（最高可达94%的对映体过量，催化剂负载量为5摩尔%）。
• Nickel-Catalyzed Enantio- and Diastereoselective Three-Component Coupling of 1,3-Dienes, Aldehydes, and a Silylborane Leading to α-Chiral Allylsilanes
  作者：Nozomi Saito、Ayami Kobayashi、Yoshihiro Sato

  DOI：10.1002/anie.201107360

  日期：2012.1.27

  Three‐in‐one: The nickel‐catalyzed asymmetric three‐component coupling of 1,3‐dienes, aldehydes, and a silylborane in the presence of a chiral phosphoroamidite ligand has been realized. The reaction proceeds by σ‐bond metathesis of an oxanickelacycle intermediate with the silylborane to afford the corresponding α‐chiral allylsilane derivative in a highly diastereo‐ and enantioselective manner.

  三合一：在手性亚磷酰胺配体的存在下，已实现了镍催化的1,3-二烯，醛和甲硅烷基硼烷的不对称三组分偶联。该反应通过氧杂ickelacycle中间体与甲硅烷基硼烷的σ键复分解而进行，从而以高度非对映和对映选择性的方式提供相应的α-手性烯丙基硅烷衍生物。
• Asymmetric Construction of an Aryl‐Alkene Axis by Palladium‐Catalyzed Suzuki–Miyaura Coupling Reaction
  作者：Sheng‐Qi Qiu、Yu Chen、Xiang‐Jun Peng、Shi‐Jiang He、Jun Kee Cheng、Yong‐Bin Wang、Shao‐Hua Xiang、Jun Song、Peiyuan Yu、Junmin Zhang、Bin Tan

  DOI：10.1002/anie.202211211

  日期：2022.11.7

  The construction of axially chiral acyclic aryl-alkene skeletons via classic Suzuki–Miyaura reaction has been challenging compared to the biaryls. Rational optimization established an enabling 3,3′-triphenylsilyl-substituted phosphite ligand for asymmetric coupling of hindered aryl halides and vinyl boronates under mild conditions, affording the acyclic aryl-alkenes in good yield, atroposelectivity

  与联芳基相比，通过经典的 Suzuki-Miyaura 反应构建轴向手性无环芳基烯烃骨架一直具有挑战性。合理的优化建立了一个 3,3'-三苯基甲硅烷基取代的亚磷酸酯配体，用于在温和条件下受阻芳基卤化物和硼酸乙烯酯的不对称偶联，以良好的收率、阻转选择性和E / Z选择性提供无环芳基烯烃。
• Chiral BINOL-based borate counterions: from cautionary tale on anion stability to enantioselective Cu-catalyzed cyclopropanation
  作者：Anthony Labelle、Bruce A. Arndtsen

  DOI：10.1039/d2cc05924j

  日期：——

  Studies on a new type of chiral BINOL-based boron counterion highlights its ability to rearrange under the reaction conditions to create a ligand that can be used in the copper-catalyzed cyclopropanation of alkenes.

  对一种新型手性BINOL基硼对离子的研究表明，它能够在反应条件下重排，生成可用于铜催化的烯烃环丙基化反应的配体。