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Updated: Jun 10, 2025

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Published on: February 6, 2019

通过非激活的电化学还原性水利化通过Dearomative循环/螺旋循环

Yi-Miao Wu¹, Xian-Li Ma^1,2, Fang-Yao Li¹

¹Guangxi Key Laboratory of Drug Discovery and Optimization, Guangxi Engineering Research Center for Pharmaceutical Molecular Screening and Druggability Evaluation, Key Laboratory of Medical and Translational Medicine, School of Pharmacy, Guilin Medical University, Guilin 541199, People's Republic of China.

Organic letters

|October 14, 2024

概括

这项研究引入了一种电化学方法来进行还原性 dearomatization,使非激活的有效循环和螺旋循环. 这种新的协议产生了具有高选择性的有价值的工业线和相关结构.

科学领域:

有机化学有机化学
电化学电化学电化学
合成方法论合成方法论

背景情况:

降低性 dearomatization 是有机合成的一个关键转换.
开发有效的循环化非激活的方法仍然具有挑战性.

研究的目的:

开发一种新的电化学协议,用于还原性 dearomatization 和随后的循环/spirocyclization.
探索这个新合成战略的范围和局限性.

主要方法:

电化学循环/螺旋循环通过还原性 dearomatization.
使用一个简单的未分割的电化学电池.
采用非活化,如N替代的英多尔,英多尔-3-碳胺衍生物和替代的胺.

主要成果:

成功合成了50种不同类型的印度林,螺旋循环化水利化产品和丁.
证明了高原子效率,广泛的基质范围和出色的选择性.
在芳香环中实现了基的分子内添加.

结论:

开发的电化学协议为复杂的循环和螺旋循环化合物提供了强大而高效的途径.
这种方法提供了一个通用的平台,可以访问有价值的醇衍生物和相关结构.

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Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

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Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.

Cycloaddition Reactions: Overview

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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.

Photochemical Electrocyclic Reactions: Stereochemistry

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Selection Rules: Photochemical Activation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
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