立体选择性基努加萨/阿尔多尔循环:合成富含乙的螺旋环β-乳酸盐
Alexa Torelli1, Eun Seo Choi1, Aurélien Dupeux1
1Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Organic letters
|November 15, 2023
概括
这项研究引入了一种新的铜催化反应,用于制造螺旋环分子. 该方法有效合成具有高立体选择性的复杂结构,为有机合成提供了新的可能性.
科学领域:
- 有机化学 有机化学
- 催化剂是一种催化剂.
- 立体选择性合成 立体选择性合成
背景情况:
- 复杂的螺旋环化合物的合成仍然是有机化学的一个挑战.
- 开发高效和立体选择性方法来构建螺旋结合环系统是非常可取的.
研究的目的:
- 为了开发一种酶选择性铜催化多米诺反应.
- 为了获得具有高立体控制的螺旋环β-乳酸pyrrolidinones.
主要方法:
- 采用了一种用铜催化的Kinugasa/aldol多米诺反应.
- 作为起始材料,使用了亲性基因结合的和.
- 在温和条件下进行的反应.
主要成果:
- 实现了两个螺旋融合环系统的轻松建造.
- 产生了含有三个连续立体中心的分子.
- 在合成中获得了出色的enantioselectivity.
结论:
- 开发的策略提供了有效的获取旋环 β-乳酸 pyrrolidinones.
- 证明了合成分子下游功能化的潜力.
相关概念视频
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
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
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
3.4K
α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
3.4K
Stereochemical Effects of Enolization
2.0K
The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound undergoes racemization under an acidic or basic condition, an achiral enol is formed.
2.0K
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
Aldol Condensation with β-Diesters: Knoevenagel Condensation
3.1K
The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.
3.1K


![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)