通过姜黄素与芳基亚甲基丙二酸酯的共轭加成，非对映选择性合成高取代的环己酮和四氢苯并吡喃-4-酮。

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2024-08-15 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.177

Deepa Nair, Abhishek Tiwari, Banamali Laha, Irishi N N Namboothiri

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引用次数: 0

摘要

本研究报道了一种级联分子间双迈克尔策略，用于从姜黄素和芳基亚甲基丙二酸酯合成高度官能化的环己酮。该方法以 TBAB 为合适的相转移催化剂，在 KOH 水溶液存在下于室温下进行。在大多数情况下，官能化环己酮作为主要产物以中等到极好的产率和完全的非对映选择性形成。在少数情况下，三迈克尔加合物--四氢苯并吡喃-4-酮也会作为副产品生成，并具有极佳的非对映选择性。

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Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates.

A cascade inter-intramolecular double Michael strategy for the synthesis of highly functionalized cyclohexanones from curcumins and arylidenemalonates is reported. This strategy works in the presence of aqueous KOH using TBAB as a suitable phase transfer catalyst at room temperature. The functionalized cyclohexanones are formed as major products in moderate to excellent yields with complete diastereoselectivity in most cases. A triple Michael adduct, tetrahydrochromen-4-one, is also formed as a side product in a few cases with excellent diastereoselectivity.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.