走向一个多功能合试剂:实用,使用应变的合环来对acylhydrazones进行选择性合,使用应力合环
Richard Berger1, Philippe M A Rabbat, James L Leighton
1Department of Chemistry, Columbia University, New York, New York 10027, USA.
Journal of the American Chemical Society
|August 9, 2003
概括
一种新方法使得使用应变的环试剂,能够对乙基化进行抗选择性化. 这种方法产生了具有高反体过剩的化物产物,可通过再结晶来分离.
科学领域:
- 有机化学 有机化学
- 不对称的合成方法
背景情况:
- 乙化素是多功能合成中间体.
- 对药品和精细化学品而言,酶选择性合成至关重要.
研究的目的:
- 开发一种实用且高效的方法,用于对乙基化的酶选择性化.
主要方法:
- 使用了一种先前报道的压缩轮试剂.
- 与各种酸和酸环试剂发生反应.
主要成果:
- 对于化物产品来说,获得了良好的至优秀的反选择活性 (83-89% ee).
- 证明产品可以通过再结晶来净化到>/=98% ee,而无需染色学.
结论:
- 开发的方法提供了一个非常实用的路径,以实现enantioselective合并.
- 高选性和简单的净化使得这种方法在合成应用中非常有价值.
相关概念视频
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Cycloaddition Reactions: Overview
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.
[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.
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.
Acid-Catalyzed Aldol Addition Reaction
The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.


