線形アルケニル (N) -アルコキシ炭酸塩をサイクルブロム炭酸塩に変換する
Shyam Sathyamoorthi1, Steven P Kelley2
1Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.
まとめ
この研究では,アルケニルN-アルコキシカルバメットから循環型ブロム炭酸を合成する簡単な方法が紹介されています. このプロセスは効率的で,スケーラブルで,様々な機能グループと互換性があり,有機合成で多用途である.
科学分野:
- 有機化学
- 合成方法論
背景:
- N-アルコキシカルバメットは,多用途の合成中間物質である.
- 循環性ブローム炭酸は有機合成における貴重な構成要素である.
研究 の 目的:
- 線形アルケニルN-アルコキシカルバメットを周期性ブロム炭酸に変換するための簡単で効率的なプロトコルを開発する.
- 多様な機能群と互換性のある 拡張可能で堅固な合成方法を確立する.
主な方法:
- 線形アルケニルN-アルコキシカルバメトとブロミン剤の反応
- 反応条件の最適化により,シンプルで効率的になります.
- 機能的群の耐性およびダイアステレオ選択性の評価
主要な成果:
- アルケニルN-アルコキシカルバマートのサイクルブローム炭酸への成功変換
- 様々な基板で高いダイアステレオ選択性を達成した.
- 操作のシンプルさ,スケーラビリティ,および幅広い機能群の互換性を実証する.
- 安価で簡単に手に入る反応剤の特定
結論:
- 開発されたプロトコルは,循環性ブローム炭酸への実用的で効率的な経路を提供します.
- この方法のスケーラビリティと機能群の許容性は,様々な合成用途に適しています.
- その結果生じる周期性ブローム炭酸は,さらなる化学的変異を受けやすい.
関連する概念動画
Halogenation of Alkenes
16.5K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
16.5K
Hydroboration-Oxidation of Alkenes
8.9K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
8.9K
Formation of Halohydrin from Alkenes
13.3K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
13.3K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
18.9K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
18.9K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
4.1K
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...
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...
4.1K
Preparation of Carboxylic Acids: Hydrolysis of Nitriles
4.7K
Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
4.7K


