非对称黄金 ((I) - 催化子类型循环,用于三环架构的建造
Aurélien Dupeux1, Emilie Gentilini1, Véronique Michelet1
1Université Côte d'Azur, Institut de Chimie de Nice, Valrose Park, 06108 Nice Cedex 2, France.
The Journal of organic chemistry
|June 9, 2023
概括
研究人员开发了一种新的黄金催化系统,用于普林斯类型的循环,实现高产量和多重选择性. 他们还报告了第一个enantioselective版本,产生高度纯净的产品.
科学领域:
- 有机化学 有机化学
- 催化剂是一种催化剂.
- 不对称的合成方法
背景情况:
- 普林斯类型的循环是构建复杂分子架构的有价值的.
- 黄金催化剂为有机转化提供了独特的反应能力.
- 在合成中,实现高的二选择性和选择性仍然是关键的挑战.
研究的目的:
- 开发一种新且高效的黄金催化系统,用于普林斯型循环.
- 报告了第一个enantioselective黄金催化普林斯型循环.
- 为了合成具有高立体化学控制的复杂分子.
主要方法:
- 使用的黄金 (I) 催化剂用于普林斯型循环反应.
- 开发了一种新的基于TADDOL的合性Au (I) 酸复合物.
- 研究反应条件以优化13个实例的产量和选择性.
主要成果:
- 开发的普林斯型循环系统的产量达到了89%.
- 成功演示了第一个对抗选择性黄金催化普林斯型循环.
- 结晶后具有高反体过剩 (>99% ee) 的产品.
结论:
- 这种新的金催化系统为复杂分子提供了一条有效的途径.
- 基于TADDOL的奇拉Au(I) 斯酸盐复合物使得高度反选择性的普林斯型循环.
- 这项工作推进了对立选择性合成的不对称催化.
相关概念视频
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
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
3.3K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.3K
Cycloaddition Reactions: Overview
2.7K
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.
2.7K
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
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
3.5K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.5K
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

![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)
