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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

4.3K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
4.3K
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

4.7K
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...
4.7K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

12.5K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
12.5K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

4.0K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
4.0K
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives01:35

Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

2.7K
Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
2.7K
Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

Aldol Condensation with β-Diesters: Knoevenagel Condensation

3.9K
The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.
3.9K

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

10.6K

デカルボキシル化アルケニル化

Jacob T Edwards1, Rohan R Merchant1, Kyle S McClymont1

  • 1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Nature
|April 21, 2017
PubMed
まとめ
この要約は機械生成です。

この研究は,容易に入手可能なアルキルカルボキシル酸から,任意のパターンまたは幾何学的なオレフィンを合成するための新しい方法を導入しています. このアプローチは,触媒による二酸化炭素流出とオルガノシン結合を用いて,オレフィン合成と天然製品の製造を簡素化しています.

さらに関連する動画

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

Published on: June 21, 2017

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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
09:14

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

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関連する実験動画

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

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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

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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

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科学分野:

  • 有機化学
  • 合成方法論
  • カタリシス

背景:

  • オレフィン化学は有機物質の操作に不可欠ですが,時代遅れの合成方法に依存しています.
  • メタテシスを含む既存のオレフィン合成技術は,しばしば限られているか,数十年前に開発された.
  • アルキルカルボキシル酸は豊富で汎用的な化学的構成要素である.

研究 の 目的:

  • 多様な置換パターンと幾何学を持つオレフィンを合成するためのシンプルで広く適用可能な方法を開発する.
  • アミド結合合成の活性化原理をカーボキシル酸の機能化に活用する
  • カーボキシル酸からオレフィン製剤を 経済的かつスケーラブルな方法で製造する.

主な方法:

  • アルキルカルボキシル酸を活性化するために,ニッケルまたは鉄ベースの触媒を用いた.
  • アミド結合合成の原理を用いて,二酸化炭素の挤出を容易にした.
  • 活性化されたカルボキシル酸誘導体とオルガノジン反応剤を結合してオレフィンを作ります.

主要な成果:

  • 60種類以上のオレフィンを 合成しました
  • オレフィン幾何学と置換パターンを制御するメソッドの能力を実証した.
  • 10つのファミリーから16の天然製品の合成によって示された,簡素化された逆合成分析.

結論:

  • アルキルカルボキシル酸から直接オレフィン合成のための新しい,効率的で汎用的な方法を提示しました.
  • 触媒的プロセスは,既存のオレフィン合成戦略に経済的かつ拡張可能な代替手段を提供します.
  • この方法論は,天然製品を含む複雑な分子の準備を大幅に簡素化します.