用于高对映选择性Aldol和oxa-Michael-Aldol级联反应的可回收螺旋l-缬氨酸聚合物催化剂

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-06-10 DOI:10.1016/j.tet.2025.134775

Zixuan Wang , Chaoxing Chen , Shuyi Wang , Chonglong Li

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引用次数: 0

摘要

设计并合成了一种新型的含l-缬氨酸的螺旋聚合物（poly-1m）吊坠。手性l-缬氨酸聚合物催化剂在Aldol反应中表现出良好的催化活性和立体选择性。聚合物poly-1200在水中催化环戊酮和4-硝基苯甲醛的Aldol反应，其对映体过量（ee）值高达97%，非对映体比（dr）为42/58。此外，手性聚合物催化剂可以在不对称Aldol加成反应中循环使用三次而不明显损失催化活性。同样的催化剂应用于肉桂醛和水杨醛的不对称oxa-Michael-Aldol级联反应，对映体过量87%。

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A recyclable helical l-Valine-polymer catalyst for highly enantioselective Aldol and oxa-Michael-Aldol cascade reactions

A novel helical polymer (poly-1_m) bearing l-Valine pendant was designed and synthesized. The chiral l-Valine polymer catalyst demonstrated excellent catalytic activity and stereoselectivity in the Aldol reaction. The polymer poly-1₂₀₀ catalyzed the Aldol reaction of cyclopentanone and 4-nitrobenzaldehyde in water, achieving an enantiomeric excess (ee) value of up to 97 % and a diastereomeric ratio (dr) of 42/58. Furthermore, the chiral polymer catalyst can be recycled three times in asymmetric Aldol addition reactions without significant loss of catalytic activity. The same catalyst was applied in the asymmetric oxa-Michael-Aldol cascade reaction of cinnamaldehyde and salicylaldehyde, achieving an enantiomeric excess of 87 %.

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来源期刊

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.