活性化されていないアルケンの高度にエナチオセレクティブのクロスエレクトロフィールアリルアルケニル化
Zhi-Xiong Tian1, Jin-Bao Qiao1, Guang-Li Xu1
1State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering , Lanzhou University , 222 South Tianshui Road , Lanzhou 730000 , China.
Journal of the American Chemical Society
|April 20, 2019
まとめ
この研究は,活性化されていないアルケンのアリルアルケニル化のための新しいエナンチオセレクティブのクロスエレクトロフィール反応を導入する. この方法は,穏やかな条件下で生物学的に重要なキラル分子を効率的に合成します.
科学分野:
- 有機化学
- カタリシス
- アシンメトリック・シンセシス
背景:
- エナチオセレクティブのクロスエレクトロフィール反応は,金属触媒に挑戦しています.
- 以前の研究では,主にラセミアルキル電粒子のステレオコンバージェント反応に焦点を当てていた.
研究 の 目的:
- 活性化されていないアルケンのためのエナチオセレクティブのクロスエレクトロフィールアリルアルケニル化反応を開発する.
- 生物学的に重要なキラル分子へのアクセスを提供します.
主な方法:
- エナチオセレクティブ・クロス・エレクトロフィール・アリル・アルケニル化のための金属触媒を用いた.
- 高いエナチオ選択性のためにキラル・ピロックス・リガンドを使用した.
- 室温で穏やかな条件下で反応を行った.
主要な成果:
- 活性化されていないアルケンのエナチオセレクティブアリルアルケニル化が成功しました.
- 合成されたキラル・ジヒドロベンゾフラン,インドリン,インダネ.
- ペプチドやステロイドのような 複雑な分子を改造することで 合成の有用性を証明した
結論:
- 開発された方法は,価値あるキラル分子への新しい経路を提供します.
- 組み込まれたアルケニル群はさらに分子多様化を可能にします.
- 反応は効率的で軽いもので,複雑な基板に適用できます.
関連する概念動画
Introduction to Electrophilic Addition Reactions of Alkenes
10.2K
The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...
Addition and elimination...
10.2K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
16.6K
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...
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...
16.6K
Electrophiles
12.7K
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
12.7K
Nomenclature of Aryl and Heterocyclic Amines
3.1K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
3.1K
Crossing Over
169.6K
Unlike mitosis, meiosis aims for genetic diversity in its creation of haploid gametes. Dividing germ cells first begin this process in prophase I, where each chromosome—replicated in S phase—is now composed of two sister chromatids (identical copies) joined centrally.
The homologous pairs of sister chromosomes—one from the maternal and one from the paternal genome—then begin to align alongside each other lengthwise, matching corresponding DNA positions in a process...
The homologous pairs of sister chromosomes—one from the maternal and one from the paternal genome—then begin to align alongside each other lengthwise, matching corresponding DNA positions in a process...
169.6K
Monohybrid Crosses
238.8K
Overview
238.8K


