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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
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One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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催化不对称的Vinylogous Prins循环:对四氨酸的高度二元选择性和反选择性输入

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  • 1Max-Planck-Institut für Kohlenforschung , Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.

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概括

研究人员开发了第一个催化不对称的普林斯循环,使得四水 (THF) 的高度选择性合成. 这种新的方法利用性二酸 (IDP) 催化剂进行高效的立体选择性循环反应.

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科学领域:

  • 有机化学
  • 不对称的催化
  • 合成方法

背景情况:

  • 四氨酸 (THF) 是天然产品和药品中普遍存在的结构图案.
  • 对于THF合成的高效和立体选择性方法仍然是有机化学的一个关键挑战.
  • 催化不对称反应为构建复杂的性分子提供了强大的工具.

研究的目的:

  • 报告第一个催化不对称的Prins循环.
  • 开发一种高度分离选择和分离选择的方法来合成替代的四.
  • 研究开发的催化系统的范围和局限性.

主要方法:

  • 设计和合成一个受限制的化二酸 (IDP) 催化剂.
  • 在芳香/异芳香和3,5--1-之间的反应中使用IDP催化剂.
  • 使用高酸度的二氧化二胺酸 (IDPi) 催化剂对酸性化物.
  • 使用DFT计算来阐明反应机制和立体选择性.

主要成果:

  • 获得高度的二元选择性 (d.r. > 20:1) 和反选择性 (e.r. 在多达99:1的时间内合成2,3-非替代的四氨酸.
  • 用芳香和异芳香的化物证明了基质的广泛范围.
  • 使用IDPI催化剂表现出优异的结果.
  • 在使用赛米二烯醇时观察到的动态分辨率.
  • DFT计算提供了有关高立体选择性起源的见解.

结论:

  • 开发的催化不对称的普林斯循环是合成立体定义四的有效方法.
  • 封闭式性IDP和IDPI催化剂在THF合成中实现了高水平的立体控制.
  • 这种方法提供了一种有价值的新工具,用于访问含有THF核心的复杂性分子.