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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

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 alkylated β-keto acid.
Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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関連する実験動画

Updated: Jun 12, 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

触媒的非対称トランザケチゼテーション.

Ilija Corić1, Sreekumar Vellalath, Benjamin List

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

Journal of the American Chemical Society
|June 10, 2010
PubMed
まとめ
この要約は機械生成です。

新しい触媒法により,キラルリン酸であるTRIPを用いたエナンチオセレクティブトランセセタライゼーションが可能です. この反応は,アセタルの非対称合成のための新しい経路を提供し,単一のステレオジェニックセンターを作成します.

さらに関連する動画

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
06:00

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

Published on: January 15, 2018

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

関連する実験動画

Last Updated: Jun 12, 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

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
06:00

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

Published on: January 15, 2018

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

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • アシンメトリック・シンセシス

背景:

  • トランサケチゼーションは,有機合成における重要な反応である.
  • アセタル形成のためのエナチオセレクティブの方法の開発は,キラル分子へのアクセスに不可欠です.

研究 の 目的:

  • 触媒的エナチオセレクティブトランセセチゼーション反応を開発する.
  • この変換の触媒としてキラルリン酸を使用する.

主な方法:

  • トリップ (キラルリン酸) を触媒として使った.
  • 触媒条件下で反応するO,O-アセタル.

主要な成果:

  • TRIPは,トランザセチ化において高い効率性とエナチオ選択性を示した.
  • この反応は,単一の立体性中心を持つアセタルを成功裏に生成した.

結論:

  • 新しい触媒的エナチオセレクティブトランセセタリゼーションが達成されました.
  • チラルリン酸TRIPは,非対称性アセタル合成の効果的な触媒である.