一个激进的程序,用于抗马尔科夫尼科夫的alkenes的化
Ajoy Kapat1, Andreas König, Florian Montermini
1Department of Chemistry and Biochemistry, University of Bern, Switzerland.
这项研究引入了一种高效的单方法,用于基化,使用化和激素启动的反应. 该过程提供了反马尔科夫尼科夫的区域选择性,对各种替代的烯有效.
科学领域:
- 有机化学 有机化学
- 合成方法论 合成方法论
背景情况:
- 基的化是有机合成中的关键转化.
- 开发高效和区域选择性方法仍然是一个活跃的研究领域.
研究的目的:
- 描述一种新的单工艺,用于高效的基化.
- 在化反应中实现反马尔科夫尼科夫的区域选择性.
主要方法:
- 一种单反应序列,涉及基因与甲基醇的化反应.
- 以后的反应与二硫亚化物在一个激素发起剂的存在下.
主要成果:
- 水力钻井步骤有效控制了区域选择性,产生了反马尔科夫尼科夫的产品.
- 该方法在各种基因中显示出广泛的适用性,包括1,2-非替代和三替代基质.
- 对于广泛的基基质,获得了优异的结果.
结论:
- 描述的单氧化方法是高效的和区域选择性的.
- 这种方法为从基中合成含化合物提供了有价值的工具.
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相关概念视频
Radical Anti-Markovnikov Addition to Alkenes: Mechanism
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy radical...
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Hydroboration-Oxidation of Alkenes
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
