銅触媒によるボリルアリレーションによる2,3-非置換アゼチドインのエナンチオセレクティブ合成
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PubMedで要約を見る
まとめ
この要約は機械生成です。この研究は,銅触媒による非対称ボリルアルキレーションを用いて,キラル2,3-非置換アゼチチドンを生成するための新しい方法を導入している. このプロセスは,高い選択性を持つ有価なアゼチジンの支架への直接的な経路を提供します.
科学分野
- 有機化学
- 非対称な触媒
- ヘテロサイクル化学
背景
- チラルの2,3-非置換アゼチジンは重要な支架ですが,一般的な合成アクセスはありません.
- アゼチジンの機能化に関する以前の方法は限られている.
研究 の 目的
- アゼチンの高度なエナチオセレクティブの機能不全を発達させる.
- キラルの2,3-非置換アゼチジンの便利なアクセスを提供するために.
主な方法
- 銅/ビスホスフィンがアゼチンの非対称ボリルアルキル化を触媒した.
- アルキル化を促進し,副作用を防ぐためにアルリルリン酸を使用した.
主要な成果
- アゼチンにボリルとアルリル群を高度にエナチオセレクティブに固定する.
- 完全な地域,エナチオ,およびダイアステレオ選択性を有するキラル2,3-非置換アゼチジンを生成した.
- ダブルボンドの構成と 機能群の互換性について 優れた制御を示した.
結論
- 開発された方法は,価値あるキラルアゼチジンの誘導体への一般的かつ効率的な経路を提供します.
- ボリルとアルリルの機能は,さらなる合成変換を可能にします.
- 反応メカニズムは,S<sub>N</sub>2′アリレーションに続くボリルカプレーションである.
関連する概念動画
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Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
However, enamines are neutral and less reactive than enolates, which bear a net negative charge. Consequently, enamines are effective Michael donors...
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
In the Curtius rearrangement, acyl azides are converted into primary amines under thermal conditions, accompanied by the loss of gaseous N2 and CO2. The loss of nitrogen acts as...