Improvement of bifunctional organocatalysts performance by water as an additive in the Michael addition of carbonyl compounds to maleimides

IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2024-09-14 DOI:10.1016/j.tet.2024.134273
Josué Vazquez-Chavez , Socorro Luna-Morales , Howard Díaz-Salazar , Diego A. Cruz-Aguilar , Marcos Hernández-Rodríguez
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Abstract

The diastereoselective Michael addition of ketones to maleimides using bifunctional organocatalysts presents a significat challenge. We developed a protocol in which the addition of 5 equivalents of water boosted the diastereoselectivity of six-membered ring ketones. However, the results were influenced by steric effects and varied outcomes were observed with different ring sizes of ketones and acyclic carbonyl compounds. The improvement in the asymmetric synthesis of succinimides due to water appears to be more related to hydrogen bonds at the interface rather than a water molecule embedded in the transition state. Additionally, we explored 3-substituted maleimides and found that only those with phenyl and phenylethynyl groups underwent the reaction. Finally, the desymmetrization of N-(2-tert-butylphenyl)maleimide generated the atropoisomer with good selectivity.

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在羰基化合物与马来酰亚胺的迈克尔加成反应中用水作为添加剂改善双功能有机催化剂的性能
使用双功能有机催化剂将酮与马来酰亚胺进行非对映选择性迈克尔加成是一项重大挑战。我们开发了一种方案,在其中加入 5 个当量的水可提高六元环酮的非对映选择性。然而,结果受到立体效应的影响,不同环大小的酮和无环羰基化合物会产生不同的结果。水对琥珀酰亚胺不对称合成的改善似乎更多地与界面上的氢键有关,而不是过渡态中嵌入的水分子。此外,我们还研究了 3-取代的马来酰亚胺,发现只有那些带有苯基和苯乙炔基的马来酰亚胺才会发生反应。最后,N-(2-叔丁基苯基)马来酰亚胺的非对称反应生成了具有良好选择性的亚拓异构体。
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来源期刊
Tetrahedron
Tetrahedron 化学-有机化学
CiteScore
3.90
自引率
4.80%
发文量
439
审稿时长
34 days
期刊介绍: Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
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