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Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
作为迪尔斯-阿尔德二烯的维нил:简要的 (-) - 氨基的简要合成
Michael A Kienzler1, Sandy Suseno, Dirk Trauner
1Department of Chemistry, University of California, Berkeley, California 94720-1460, USA.
Journal of the American Chemical Society
|June 14, 2008
概括
开发了一种新的 (-) - - 氨基的不对称合成方法. 这种高效的方法利用二分体选择性赫克循环和分子内反向电子需求迪尔斯-阿尔德反应来构建复杂的分子架构.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- (-) 氨基是一种具有潜在生物活性的天然产品.
- 有效和立体选择性合成路径对于获得复杂的自然产品至关重要.
研究的目的:
- 为了开发一个简洁和不对称的 (-) - - 氨的合成.
- 建立一种新的合成策略,采用关键的C-C键形成反应.
主要方法:
- 不对称的合成方法
- 灾难选择性赫克循环形成一个四元中心.
- 内部分子反向电子需求迪尔斯-阿尔德反应与乙烯基子反应.
主要成果:
- 实现了 (-) - 氨酸的高度融合合成.
- 合成成功地设置了一个四级立体中心.
- 需要最小限度地使用保护组.
结论:
- 开发的合成途径是高效和立体选择性的.
- 这种方法为合成 (-) - - 氨酸和相关化合物提供了有价值的方法.
相关概念视频
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Preparation of Alkynes: Dehydrohalogenation
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
Electrophilic Addition to Alkynes: Hydrohalogenation
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
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.
Diels–Alder Reaction: Characteristics of Dienes
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...

