Unlocking the Phosphoric Acid Catalyzed Asymmetric Transfer Hydrogenation of 2-Alkenyl Quinolines for Efficient Flow Synthesis of Hancock Alkaloids

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-03-21 DOI:10.1021/acs.orglett.5c00842

Bence S. Nagy, Aitor Maestro, Miquel A. Pericàs, C. Oliver Kappe, Sándor B. Ötvös

引用次数: 0

Abstract

Chiral tetrahydroquinolines are present in several bioactive molecules, such as the Hancock alkaloids. Although the organocatalytic asymmetric transfer hydrogenation of 2-aryl quinolines has emerged as a safer alternative to using hydrogen gas, analogous reactions with 2-alkenyl quinolines remain unexplored. Here we present a protocol to synthesize key enantioenriched intermediates to the Hancock alkaloids, providing a constant outcome for, at least, a 24 h continuous flow operation.

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磷酸催化2-烯基喹啉不对称转移加氢高效流动合成汉考克生物碱

手性四氢喹啉存在于多种生物活性分子中，例如汉考克生物碱。虽然 2-芳基喹啉的有机催化不对称转移氢化反应已成为使用氢气的更安全的替代方法，但 2-烯基喹啉的类似反应仍有待探索。在此，我们提出了一种合成汉考克生物碱关键对映体中间体的方案，该方案可在至少 24 小时的连续流动操作中提供稳定的结果。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.