通过协奏组 [4 + 2] - 循环添加/芳香反应构建取消的Spiro[4.4]-nonane-diones
Konstantin S Ivanov1, Denis E Samburskiy1, Leila V Zargarova1,2
1Laboratory of Low-carbon Chemical Technologies, ORËL Research Lab, Novosibirsk State University, Novosibirsk 630090, Russia.
The Journal of organic chemistry
|July 18, 2023
概括
一种新的迪尔斯-阿尔德反应方法合成了合的spiro[4.4]-nonane-dione衍生物. 这种高效的过程涉及螺旋基和活性基,使得可以产生对称和不对称的化合物.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- 螺旋环化合物是药物化学中有价值的支架.
- 化螺旋[4.4]-诺安-衍生物的高效合成仍然是一个挑战.
研究的目的:
- 开发一种用于合成对称和不对称的合螺旋[4.4]-纳-二离子衍生物的多功能方法.
- 探索Diels-Alder反应在构建复杂的螺旋环系统中的实用性.
主要方法:
- 使用迪尔斯-阿尔德反应,使用spiro[4.4]nona-2,7-diene-1,6-dione作为二氧化物.
- 使用四博烯/NaI,1,3-二化/BF3或替代旋风生成的活性二烯成分.
- 立即进行了Diels-Alder adduct的芳香化.
主要成果:
- 成功合成了对称和不对称的合螺旋[4.4]-nonane-dione衍生物.
- 证明了开发的Diels-Alder战略的广泛适用性.
- 展示了各种二烯基发电系统的有效性.
结论:
- 开发的迪尔斯-阿尔德反应提供了一条有效的途径,以获得多种融合的螺旋[4.4]-诺南-衍生物.
- 这种方法为访问复杂的螺旋环结构提供了有价值的工具.
- 合成策略是适应和高效的各种二烯和二烯基组合.
相关概念视频
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
10.3K
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.
10.3K
Cycloaddition Reactions: Overview
2.6K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.6K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
2.2K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.2K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
3.9K
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.
3.9K
Cycloaddition Reactions: MO Requirements for Thermal Activation
3.6K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
3.6K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
4.7K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.7K

![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
