化 (3 + 2) 循环添加室内物,用于完全功能化的环类的立体选择性组装
Amjad Ayad Qatran Al-Khdhairawi1, Tengrui Yuan1,2, Kristof Van Hecke3
1Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, B-9000 Ghent, Belgium.
Organic letters
|May 2, 2024
概括
金 (((I) 催化使使用2-乙-1,3-二硫乙的醇可进行芳香性环取. 这种方法可以创建具有高度控制的多个立体中心,允许进一步合成复杂的环丹.
科学领域:
- 有机化学 有机化学
- 催化剂是一种催化剂.
- 合成方法论 合成方法论
背景情况:
- 印衍生物是药物化学中的关键支架.
- 结合印醇的立体化学丰富的环丹环的高效构造仍然是一个合成挑战.
研究的目的:
- 开发一种新的黄金 (I) 催化反应,用于印的 dearomative cyclopentannulation.
- 在形成新的立体中心中实现高立体控制.
- 为了探索由此产生的循环丹融合的印度林的合成实用性.
主要方法:
- 黄金 (((I) 催化反应在各种醇和2-乙-1,3-二甲基之间.
- 对产品进行立体化学分析.
- 在随后的合成转化过程中,循环坦融合了印度林.
主要成果:
- 这种反应有效地从英多尔和2-乙-1,3-二甲醇中形成环丹融合的印度林.
- 产生了三个新的立体中心,具有出色的相对立体化学控制.
- 这种方法可以容忍道基板上的多种功能组.
- 进一步的操纵允许合成完全替代的环丹,控制五个立体中心.
- 在金 ((I) 催化反应中阐明了2-乙-1,3-二甲醇的机械二分法.
结论:
- 已经建立了一种通用的黄金 (I) 催化 dearomative 环胺注策略.
- 这种方法可以访问复杂的立体定义的环丹融合的印林结构.
- 这项研究提供了关于黄金 (I) 催化反应的机制的见解,其中涉及2-乙-1,3-二硫.
相关概念视频
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
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
10.1K
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.
10.1K
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
3.5K
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.
3.5K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K
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

![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)
