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SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not observed.
Prochirality02:05

Prochirality

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...
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

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Updated: May 15, 2026

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

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ステレオセレクティブのアクリラート挿入のコンセプト

Boris Neuwald1, Lucia Caporaso, Luigi Cavallo

  • 1Chair of Chemical Materials Science, Department of Chemistry, University of Konstanz, 78464 Konstanz, Germany.

Journal of the American Chemical Society
|December 22, 2012
PubMed
まとめ
この要約は機械生成です。

この研究では,パラジウム複合体をフォスフィネスルフォナートリガンドで合成し,リガンドの柔軟性とステリック・バルク・インパクト・ステレオコントロールがメチルアクリラート挿入に作用することを明らかにした. 非対称リガンドは初期ステレオ選択性を高めますが,連続した挿入は,競合するステレオ制御要因のために制御が低下しています.

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Stereolithographic 3D Printing with Renewable Acrylates
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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
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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

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Last Updated: May 15, 2026

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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

科学分野:

  • 有機金属化学 有機金属化学
  • カタリシス カタリシス カタリシス
  • リガンドデザインはリガンドデザインです.

背景:

  • フォスフィネスルフォナートリガンドを含むパラジウム複合体は,触媒的応用のために調査されています.
  • リンガンドダイナミクスとステリック効果を理解することは,触媒的結果の制御に不可欠です.
  • 挿入反応におけるステレオ制御は,触媒における重要な課題であり続けています.

研究 の 目的:

  • 新種のフォスフィネスルフォナートリガンドとそのパラジウム複合体を合成し,特徴づけること.
  • リガンド構造,特にステリック・バルクと対称性が分子運動とダイナミクスに及ぼす影響を調査する.
  • パラジアム-メチル結合へのメチルアクリラート挿入のステレオ選択性を解明し,このプロセスを支配する要因を理解する.

主な方法:

  • さまざまな対称および非対称のフォスフィネスルフォナートリガンドおよびパラジウム複合体の合成.
  • 変数温度によるNMR研究と線形分析により,分子運動を検出し,エネルギーバリアを決定します.
  • in situ NMRと密度関数理論 (DFT) の計算を使用してメチルアクリラート挿入のステレオ選択性の調査.

主要な成果:

  • パラジウム複合体とフォスフィネスルフォナートリガンドの合成が成功しました.
  • リガンドと複合体におけるアリル回転は高エネルギーバリア (44-64 kJ/mol) を示し,ステリック・バルクはこれらのバリアを増加させた.
  • リガンド置換パターンは,最初のメチルアクリラート挿入に著しく影響し,非対称リガンドで6:1までのステレオ選択性を達成し,連続した挿入ではステレオ選択性が低下した.

結論:

  • リンガンドの柔軟性とステリック塊は,触媒性能に影響を与える重要な要因であり,塊の増加は挿入率と地域選択性を阻害する.
  • 非対称なフォスフィネスルフォナートリガンドは,最初の挿入ステップで高いステレオ選択性を提供することができます.
  • 連続した挿入におけるステレオ選択性の低下は,競合するエナチオモルフィックおよびチェーンエンドのステレオ制御メカニズムに起因し,制御を改善するためにさらなる概念的開発を必要とします.