用3 - 氧辛多尔对化物进行催化酶选择性化
Zhen Li1, Xiao-Ming Zhang1, Fu-Min Zhang1
1State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
Organic letters
|September 27, 2023
概括
一种新方法使得使用新型催化剂实现了对比的合成丰富的氧化醇. 这种方法产生复杂的C3四元氧化物,并有助于构建类结构.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 药用化学 医学化学
背景情况:
- 氧化醇是天然产品和药品中至关重要的异环基架.
- 开发C3四等氧化的enantioselective方法在合成上具有挑战性.
- 类型的类化合物具有复杂的三环结构,具有潜在的生物活性.
研究的目的:
- 开发一种新型的不对称的合加法,用于合成富含C3四元氧化的C3四元氧化.
- 通过*o*-azaxylylene中间体利用3-bromooxindoles和化物.
- 应用开发的方法来构建水胺类类化合物的核心结构.
主要方法:
- 不对称的并联加法反应.
- 采用从3 - - 氧醇中产生的* - - 氧烯中间体.
- 使用一种新型的螺旋-罗利丁 (SPD) 衍生双功能*N*-硫化胺催化剂.
主要成果:
- 实现了高度分类选择性和分离选择性转换.
- 合成了一系列丰富的C3四级氧化物和多种β-化物附属物.
- 证明了该方法在构建三环原子核中的方法的实用性.
结论:
- 开发的方法提供了有效的获取有价值的C3四级氧化物.
- 新型的SPD衍生催化剂是观察到的高立体选择性的关键.
- 这种方法为合成复杂的类化合物和相关化合物提供了强大的工具.
相关概念视频
Radical Anti-Markovnikov Addition to Alkenes: Overview
3.4K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
3.4K
Hydroboration-Oxidation of Alkenes
8.3K
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.
8.3K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
18.2K
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.
18.2K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
10.3K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.3K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
3.8K
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...
3.8K
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
4.2K
Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...
The carbonyl center is...
4.2K


