Jove
Visualize
お問い合わせ
JoVE
x logofacebook logolinkedin logoyoutube logo
JoVEについて
概要リーダーシップブログJoVEヘルプセンター
著者向け
出版プロセス編集委員会範囲と方針査読よくある質問投稿
図書館員向け
推薦の声購読アクセスリソース図書館諮問委員会よくある質問
研究
JoVE JournalMethods CollectionsJoVE Encyclopedia of Experimentsアーカイブ
教育
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab Manual教員リソースセンター教員サイト
利用規約
プライバシーポリシー
ポリシー

関連する概念動画

Stereochemical Effects of Enolization01:12

Stereochemical Effects of Enolization

2.0K
The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound undergoes racemization under an acidic or basic condition, an achiral enol is formed.
2.0K
Reactivity of Enols01:18

Reactivity of Enols

2.9K
Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is...
2.9K
Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

2.5K
As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
2.5K
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

3.2K
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
3.2K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.2K
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...
3.2K
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

3.3K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
3.3K

こちらも読む

関連記事

共著者、ジャーナル、引用グラフによってこの研究に関連する記事。

並び替え
Same author

Vicinal disubstitution of alkyl C-X synthons via alkene radical cation generation.

Science (New York, N.Y.)·2026
Same author

Female reproductive impacts of emerging cyanobacterial harmful algal bloom toxins.

The Journal of reproduction and development·2026
Same author

Discovery and analytical assessment of urinary miRNA biomarkers for cervical cancer using advanced small RNA sequencing.

Translational oncology·2026
Same author

Copper-catalysed site-selective arylation of pyrazoles.

Nature chemistry·2026
Same author

Genetic Characterization and Zoonotic Potential of <i>Cryptosporidium</i> spp. and <i>Giardia duodenalis</i> in Cattle From Northeast China.

Transboundary and emerging diseases·2026
Same author

Photoredox-Neutral Platform for Direct Decarboxylative Cyclopropanation <i>via</i> Acridine-Iron Dual Catalysis.

ACS catalysis·2026

関連する実験動画

Updated: May 19, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

7.3K

ダイナミック・キネティック・アシンメトリック・水酸化:ソフト・エノライゼーションによるラセミゼーション

Mengfei Xu1, Stephanie A Corio2, Josephine M Warnica1

  • 1Department of Chemistry, University of California, Irvine, California 92697, United States.

Journal of the American Chemical Society
|April 29, 2025
PubMed
まとめ

この研究は,アルデヒドから有価な1,4-ケトアミドを生成するための動的運動非対称変換 (DyKAT) を導入する. Rh触媒による水酸化は高い選択性を達成し,新しいステレオ収束C-C結合形成戦略を提供します.

さらに関連する動画

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

8.8K
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

12.9K

関連する実験動画

Last Updated: May 19, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

7.3K
Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

8.8K
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

12.9K

科学分野:

  • 有機化学
  • カタリシス
  • 非対称合成

背景:

  • ダイナミック・キネティック・アシンメトリック・トランスフォーメーション (DyKAT) は,ラセミクスの原材料をエナティオメリックに濃縮した製品に変換することを可能にします.
  • 分子間水酸化は強力なC−C結合形成反応であるが,DYKATにおけるその応用は未熟である.
  • ステレオコンバージェント触媒は,複数のステレオセンターを同時に変換することによって,キラル合成の効率を最大化することを目的としています.

研究 の 目的:

  • 1,4-ケトアミドのエナチオセレクティブ合成のための新しいダイナミック・キネティック・アシンメトリック変換 (DyKAT) の開発.
  • ラセミアルデヒドとアクリラミドのRh触媒による分子間水酸化を調査する.
  • アルデヒドのラセミ化経路を含むメカニズムを明らかにするために,DFTと実験的研究を使用します.

主な方法:

  • ダイナミック・キネティック・アシンメトリック変換 (DyKAT)
  • ロジウム触媒による水酸化
  • 分子間反応
  • DFT計算について
  • 運動解像度

主要な成果:

  • ラセミアルデヒドとアクリラミドのDyKATをRh触媒を用いて成功させた.
  • 1,4-ケトアミドの形成で達成された高いエナンチオおよびダイアステレオ選択性.
  • アルデヒドのラセミ化のための予期せぬRh触媒経路の特定.
  • 分子間水酸化による画期的な運動解像度の実証.

結論:

  • この研究は,優れたステレオ制御で1,4-ケトアミドを合成するための新しいDYKATを確立しています.
  • この発見は,ステレオ収束触媒とC−C結合構築の分野に大きく貢献する.
  • 機械学的洞察は,関連する触媒システムのさらなる開発のための基盤を提供します.