疏水口袋型有机催化：新型立体定向二苯乙二胺-异甜菊醇硫脲在绿色水溶液条件下加速迈克尔加成

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-06-06 DOI:10.1016/j.tetlet.2025.155689

Yuxia Liu, Mingyang Lv, Zhaoyang Fan, Qi Liu, Xinyu Dai

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引用次数: 0

摘要

将手性1,2-二苯乙二胺（DPEN）单元加入到异戊二醇衍生的硫脲有机催化剂中，以促进在水介质中将醛加成到马来酰亚胺。在中性条件下，新开发的isosteviolo - dpen硫脲催化剂表现出优异的性能。它不仅能提供高收率的Michael加成产物，可达98%，而且具有显著的对映选择性，最高可达99%。重要的是，这种催化剂实现了反应的双重立体选择控制，确保了产物的形成具有精确的立体化学构型。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Hydrophobic-pocket-enabled organocatalysis: New stereodirecting diphenylethylenediamine-isosteviol thioureas for accelerated michael addition under green aqueous conditions

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Hydrophobic-pocket-enabled organocatalysis: New stereodirecting diphenylethylenediamine-isosteviol thioureas for accelerated michael addition under green aqueous conditions

A chiral 1,2-diphenylethylenediamine (DPEN) unit was incorporated into an isosteviol-derived thiourea organocatalyst to facilitate the Michael addition of aldehydes to maleimides in an aqueous medium. Operating under neutral conditions, the newly developed isosteviol-DPEN thiourea catalyst demonstrates exceptional performance. It not only affords Michael addition products in high yields, with values reaching up to 98 %, but also exhibits remarkable enantioselectivities, which can go as high as 99 %. Importantly, this catalyst achieves dual stereoselective control of the reaction, ensuring the formation of products with precise stereochemical configurations.

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.