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関連する概念動画

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

4.0K
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...
4.1K
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.
2.4K
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.
9.3K
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...
5.3K
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...
5.1K

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関連する実験動画

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

一般的触媒非対称プリンスサイクル

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
まとめ

新しいイミノイミドジフォスファート (iIDP) ブロンステッド酸は不対称なプリンス循環を可能にします. この効率的な触媒法により 機能化されたテトラヒドロピランが得られ ローズオキシドのような香水の合成に役立ちます

科学分野:

  • 有機化学
  • キャタリシス
  • アシンメトリック・シンセシス

背景:

  • プリンス循環はテトラヒドロピラン構造の形成の鍵となる反応である.
  • この変換のための効率的でエナチオセレクティブな方法の開発は,有機合成における重要な課題です.

研究 の 目的:

  • 高い酸性を持つ閉じ込められたイミノイミドジフォスファート (iIDP) の新種を導入する.
  • アルデヒドの不対称なプリンス循環のためにこれらの触媒を使用する.

主な方法:

  • イミノイミドジフォスファート (iIDP) ブロンステッド酸を触媒として使用する.
  • 触媒条件下でアリファティックおよびアロマティックアルデヒドを反応させ,プリンス循環を促進する.
  • 反応産物の産量,地域,およびエナチオ選択性を分析する.

主要な成果:

  • 多様な機能化された4-メチレンテトラヒドロピランの良好から優れた生産性を達成した.
  • サイクライゼーション製品における良好から優れた地域選択性およびエナチオ選択性を示した.
  • ローズオキシドとドレモックスを含む香水化合物の合成にiIDP触媒を成功させた.

結論:

さらに関連する動画

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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関連する実験動画

Last Updated: Mar 16, 2026

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

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

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  • 開発されたiIDPブロンステッド酸は,不対称なプリンス循環のための効果的な触媒の新しいクラスを表しています.
  • この方法論は,有価なテトラヒドロピラン誘導体への効率的でスケーラブルなエナンチオセレクティブ経路を提供します.
  • 触媒システムは重要な香水分子の合成に適用できます.