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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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...
4.0K
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

4.1K
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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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.4K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.3K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Prochirality02:05

Prochirality

5.3K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.1K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Updated: Mar 16, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

13.8K

一个一般的催化不对称的普林斯循环

Luping Liu1, Philip S J Kaib1, Aurélien Tap1

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

Journal of the American Chemical Society
|August 23, 2016
PubMed
概括

新的伊米诺-伊米多二酸 (iIDP) 能够实现不对称的普林斯循环. 这种高效的催化方法可以产生功能化的四,

科学领域:

  • 有机化学
  • 催化剂
  • 不对称的合成

背景情况:

  • 普林斯循环反应是形成四烯结构的关键反应.
  • 在有机合成中,开发高效和对酶选择性的转化方法仍然是一个重大挑战.

研究的目的:

  • 引入一种新型的高酸性封闭型胺基二酸 (iIDP) 布伦斯特德酸.
  • 用这些催化剂进行非对称的阿尔德循环.

主要方法:

  • 使用封闭型胺基二酸 (iIDP) 作为催化剂.
  • 在催化条件下反应的阿利法和芳香化物以促进普林斯循环.
  • 分析反应产品的产量,区域性和反选择性.

主要成果:

  • 实现各种功能化的4-甲基四胺的良好至优异产量.
  • 在循环化产品中表现出良好的区域和反选择性.
  • 成功地将iIDP催化剂应用于香料化合物的合成, 包括氧化物和多雷莫克斯.

结论:

  • 开发的iIDP布伦斯特德酸代表了对不对称普林斯循环的新一类有效催化剂.
  • 这种方法提供了有效和可扩展的酶选择性途径,以获得有价值的四基衍生物.

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Last Updated: Mar 16, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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  • 催化系统适用于重要香料分子的合成.