经由氮杂邻联烯醌中间体合成轴手性化合物的研究进展

doi:10.6023/cjoc202305033

摘要/Abstract

轴手性化合物不仅是不对称合成领域重要的催化剂和配体, 许多天然产物和药物也是轴手性化合物. 因此, 发展轴手性化合物的高效合成方法是有机化学的重要研究课题. 相对已经被广泛研究的邻联烯醌中间体, 基于氮杂邻联烯醌中间体的不对称催化反应近年来才受到人们的关注, 研究相对较少, 有着很大的发展空间. 总结了经由氮杂邻联烯醌中间体构建轴手性化合物的研究进展, 介绍了反应范围、机理和合成应用. 最后对该研究领域的发展前景进行了总结和展望.

关键词: 氮杂邻联烯醌中间体, 轴手性化合物, 不对称催化

Axially chiral compounds are not only important catalysts and ligands in the field of asymmetric synthesis, but also widely exist in many natural products and drugs. Therefore, the development of efficient synthesis of axially chiral compounds has been an important research topic in organic chemistry. Compared with the widely studied vinylidene o-quinone methide (o-VQM) intermediates, the asymmetric catalytic reaction based on the aza-o-VQM intermediates has only attracted people’s attention in recent years, with relatively fewer studies and great potential for development. The progress in the construction of axial chiral compounds through aza-o-VQM intermediates is summarized, and the reaction type, mechanism and synthetic applications are introduced. At last, the prospect of this field is also discussed.

Key words: aza-vinylidene o-quinone methide intermediates, axially chiral compounds, asymmetric catalysis

引用此文

姜权彬. 经由氮杂邻联烯醌中间体合成轴手性化合物的研究进展[J]. 有机化学, 2024, 44(1): 159-172.

Quanbin Jiang. Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 159-172.

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图/表 14

图1. 若干轴手性天然产物、生物活性分子、配体和催化剂

Figure 1. Selected examples of axially chiral natural products, bioactive molecules, ligands and organocatalysts

图式1. 形成手性氮杂邻联烯醌中间体

Scheme 1. Generation of chiral of aza-o-VQMs

图式2. 反应的合理设计及可能路径

Scheme 2. Rational design and possible pathway of the reaction

图式3. 2-萘酚对氮杂邻联烯醌中间体的亲核加成反应

Scheme 3. Nucleophilic addition of 2-naphthols to aza-o-VQMs intermediates

图式4. 吲哚对氮杂邻联烯醌中间体的亲核加成反应

Scheme 4. Nucleophilic addition of indoles to aza-o-VQMs intermediates

图式5. 轴手性产物的合成应用

Scheme 5. Synthetic applicability of axially chiral products

图式6. 4-羟基氧杂茶邻酮对氮杂邻联烯醌中间体的亲核加成反应

Scheme 6. Nucleophilic addition of 4-hydroxycoumarins to aza-o-VQMs intermediates

图式7. 可能的反应机理

Scheme 7. Proposed reaction mechanism

图式8. 经由氮杂邻联烯醌中间体的硫化碳环化反应

Scheme 8. Thiocarbocyclization through aza-o-VQMs intermediates

图式9. 轴手性胺基硫化物的进一步转化

Scheme 9. Further transformations of axially chiral amino sulfides

图式10. 可能的反应机理

Scheme 10. Proposed reaction mechanism

图式11. 经由氮杂邻联烯醌中间体的杂环化反应

Scheme 11. Heteroannulation through aza-o-VQMs intermediates

图式12. 控制实验和可能的反应机理

Scheme 12. Control experiments and proposed reaction mechanism

图式13. 产物的衍生化

Scheme 13. Derivatization of products

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