Contrasting Facial Selectivity of a Squaramide‐Tagged Proline in the Asymmetric Michael Addition of Ketones to Maleimides

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI:10.1002/adsc.202400791

Kiran Kumari , Akram Gulam Hussain Khan , Srinivasan Easwar

引用次数: 0

Abstract

A squaramide moiety was introduced at the C‐4 position of proline to afford an organocatalyst that served as a stereocontrol element to promote the asymmetric Michael addition of cyclic ketones to maleimides. A variety of chiral succinimides were obtained by the conjugate addition in 84–98% yield accompanied by 58–96% enantioselectivity. The results also include an interesting contrast in the facial selectivity observed with cyclohexanones and cycloheptanones, whereas an asymmetric desymmetrization of 4‐alkyl cyclohexanones was also achieved using the transformation.

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Squaramide 标记的脯氨酸在酮与马来酰亚胺的不对称迈克尔加成中的对比面选择性

在脯氨酸的 C-4 位引入了一个方酰胺分子，从而获得了一种有机催化剂，该催化剂可作为立体控制元件，促进环酮与马来酰亚胺的不对称迈克尔加成反应。通过共轭加成得到了多种手性琥珀酰亚胺，产率为 84-98%，对映选择性为 58-96%。研究结果还发现，环己酮和环庚酮的面选择性形成了有趣的对比，而 4-烷基环己酮的不对称非对称化也是通过这种转化实现的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

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