钌催化的 1,7-炔的区域选择性串联环异构化/Diels-Alder 反应

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-21 DOI:10.1002/adsc.202401157

Ravichandran Logeswaran, Masilamani Jeganmohan

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引用次数: 0

摘要

本研究介绍了一种钌催化的方法，用于 1,7-enynes 的区域选择性环异构化和串联 Diels-Alder 反应，从而能够多用途合成具有四个立体中心的各种多环杂环。这种立体选择性方案与各种取代的炔烃和烯烃具有良好的兼容性，能以 46-90% 的产率获得产物，同时还能耐受各种官能团，包括酯、酮和卤化物。值得注意的是，与萘醌的反应在最终产物中保留了作为各种天然产品和生物活性化合物重要核心结构的分子。

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Ruthenium‐Catalyzed Regioselective Tandem Cycloisomerization/Diels‐Alder Reaction of 1,7‐Enynes

A ruthenium‐catalyzed methodology for regioselective cycloisomerization and tandem Diels‐Alder reactions of 1,7‐enynes has been described, enabling the versatile synthesis of diverse polycyclic heterocycles with four stereocenters. This stereoselective protocol demonstrates excellent compatibility with various substituted enynes and alkenes, yielding products in 46–90% yields while tolerating a wide range of functional groups, including esters, ketones, and halides. Notably, the reaction with naphthoquinones retains the moiety in the final product, which acts as essential core structures in various natural products and bioactive compounds.

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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

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.