(R)-(+)-1-benzyloxy-1-henyl-2-propene

• 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: (R)-(+)-1-benzyloxy-1-henyl-2-propene
• 英文别名: (R)-1-phenyl-1-benzyloxyprop-2-ene；(R)-(1-(benzyloxy)allyl)benzene；(+)-(1-benzyloxyallyl)benzene；[(1R)-1-phenylmethoxyprop-2-enyl]benzene
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: FVEFVICIKRHZCR-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-苯基丙-2-烯-1-醇 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride copper(l) iodide 、 (R)-chiral phosphoramidite 、 四丁基硫酸氢铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (R)-(+)-1-benzyloxy-1-henyl-2-propene
  参考文献：
  名称：

  铱催化的脂肪族醇盐分子间烯丙基醚化反应：二氢吡喃和二氢呋喃的不对称合成。

  摘要：

  DOI：

  10.1002/anie.200460214

文献信息

• Kinetic Resolution of Racemic and Branched Monosubstituted Allylic Acetates by a Ruthenium-Catalyzed Regioselective Allylic Etherification
  作者：Toru Shinozawa、Shou Terasaki、Shota Mizuno、Motoi Kawatsura

  DOI：10.1021/acs.joc.6b00939

  日期：2016.7.1

  of racemic and branched monosubstituted allylic acetates by a ruthenium-catalyzed regioselective allylic etherification. The reaction was effectively catalyzed by the chiral ruthenium catalyst, which was generated by [RuCl2(p-cymene)]2 and (S,S)-iPr-pybox and a catalytic amount of TFA, and both the allylic etherification product and recovered allylic acetate were obtained as an enantiomerically enriched

  我们证明了钌催化的区域选择性烯丙基醚化的外消旋和支链单取代的烯丙基乙酸酯的动力学拆分。通过[RuCl 2（p- cymene）] 2和（S，S）-iPr-pybox以及催化量的TFA生成的手性钌催化剂有效地催化了该反应，并同时回收了烯丙基醚化产物获得对映体富集形式的乙酸烯丙酯，其值最高为103 s。
• Rhodium-Catalyzed Enantioselective Intermolecular Hydroalkoxylation of Allenes and Alkynes with Alcohols: Synthesis of Branched Allylic Ethers
  作者：Zi Liu、Bernhard Breit

  DOI：10.1002/anie.201603538

  日期：2016.7.11

  Regio‐ and enantioselective additions of alcohols to either terminal allenes or internal alkynes provides access to allylic ethers by using a RhI/diphenyl phosphate catalytic system. This method provides an atom‐economic way to obtain chiral aliphatic and aryl allylic ethers in moderate to good yield with good to excellent enantioselectivities.

  通过末端Rh I /二苯基磷酸酯催化系统，将醇的区域和对映体选择性加成到末端异戊烯或内部炔烃中，即可获得烯丙基醚。该方法提供了一种原子经济的方法，可以以中等至良好的收率以及良好至优异的对映选择性获得手性脂肪族和芳基烯丙基醚。
• Enantioselective Allylic Etherification: Selective Coupling of Two Unactivated Alcohols
  作者：Markus Roggen、Erick M. Carreira

  DOI：10.1002/anie.201007716

  日期：2011.6.6

  An Ir(P,alkene) complex catalyzes the enantioselective allylic etherification of unactivated secondary allylic alcohols. Useful levels of enantioselectivity and yield were achieved with this operationally easy and robust protocol. Initial kinetic studies indicate a significant rate difference for the substrate enantiomers, allowing for a resolution process. cod=1,5‐cyclooctadiene

  Ir（P，烯烃）络合物催化未活化的仲烯丙基醇的对映选择性烯丙基醚化。通过这种操作简单，功能强大的方案，可以达到有用的对映选择性和产率水平。最初的动力学研究表明底物对映异构体的速率存在显着差异，从而可以实现拆分过程。鳕鱼= 1,5-环辛二烯
• Enantioconvergent Palladium‐Catalyzed Alkylation of Tertiary Allylic C−H Bonds
  作者：Zhong‐Sheng Nong、Xin‐Ran Chen、Pu‐Sheng Wang、Xin Hong、Liu‐Zhu Gong

  DOI：10.1002/anie.202312547

  日期：2023.11.13

  phosphoramidite-catalyzed intermolecular enantioconvergent alkylation of racemic tertiary allylic C−H bonds provides facile access to a range of enantioenriched allylic compounds featuring quaternary carbon stereocenters. The deracemization has been accomplished through a rate-limiting cleavage of racemic tertiary allylic C−H bonds to generate σ-allyl-Pd species, and the obtained E/Z-selectivity of σ-allyl-Pd species

  Pd-手性亚磷酰胺催化的外消旋叔烯丙基 C-H 键的分子间对映会聚烷基化可以方便地获得一系列具有季碳立构中心的对映体富集的烯丙基化合物。去消旋化是通过外消旋叔烯丙基 C−H 键的限速裂解生成 σ-烯丙基-Pd 物质来完成的，并且所获得的σ-烯丙基-Pd 物质的E/Z选择性通过亲核试剂显着调节非对映选择性协调启用的 S N 2′-烯丙基化途径。
• Ir‐Catalyzed Enantioselective Synthesis of <i>gem</i>‐Diborylalkenes Enabled by 1,2‐Boron Shift
  作者：Jian‐Fei Ge、Xi‐Zhang Zou、Xin‐Ru Liu、Chong‐Lei Ji、Xin‐Yuan Zhu、De‐Wei Gao

  DOI：10.1002/anie.202307447

  日期：2023.8.7

  Asymmetric cross‐couplings based on 1,2‐carbon migration from B‐ate complexes have been developed efficiently to access valuable organoboronates. However, enantioselective reactions triggered by 1,2‐boron shift have remained to be unaddressed synthetic challenge. Here, Ir‐catalyzed asymmetric allylic alkylation enabled by 1,2‐boron shift was developed. In this reaction, we disclosed that excellent enantioselectivities were achieved through an interesting dynamic kinetic resolution (DKR) process of allylic carbonates at the elevated temperature. Notably, the highly valuable (bis‐boryl)alkenes have enabled an array of diversifications to access versatile molecules. Extensive experimental and computational studies were conducted to elucidate the reaction mechanism of DKR process and clarify the origin of excellent enantioselectivities.

  摘要 基于 1,2 碳从 B-酸络合物中迁移的不对称交叉耦合反应已被有效地开发出来，以获得有价值的有机硼酸盐。然而，由 1,2-硼转移引发的对映选择性反应仍是尚未解决的合成难题。在此，我们开发了由 1,2-硼转移引发的 Ir 催化不对称烯丙基烷基化反应。在这一反应中，我们发现通过在高温下对烯丙基碳酸酯进行有趣的动态动力学解析（DKR），实现了极佳的对映选择性。值得注意的是，高价值的（双硼烷基）烯烃已经实现了一系列多样化的多功能分子。为了阐明 DKR 过程的反应机理和获得优异的对映选择性，我们进行了广泛的实验和计算研究。