光诱导NHC催化[4 + 2]环立体选择性合成吡喃[2,3-c]吡唑酮衍生物。

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-05-09 DOI:10.1039/d5ob00586h

Siyan Miao , Xian Li , Yao Chen , Chenxia Yu , Jiaomei Wang , Changsheng Yao , Kai Zhang

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引用次数: 0

摘要

本文通过光诱导n -杂环碳（NHC）催化4-芳基吡唑酮和α-重氮酮的不对称[4 + 2]环加成，合成了手性吡唑酮[2,3-c]邻叔碳和季碳立体中心衍生物，收率中等至较高，具有良好的对映选择性和非对映选择性（24例，产率高达93%，ee 95%, > 20:1 dr）。该工艺具有反应条件温和、效率高、底物范围广等特点。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Stereoselective synthesis of pyrano[2,3-c]pyrazolone derivatives via light-induced NHC catalyzed [4 + 2] annulations†

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Stereoselective synthesis of pyrano[2,3-c]pyrazolone derivatives via light-induced NHC catalyzed [4 + 2] annulations†

Herein, chiral pyrano[2,3-c]pyrazolone derivatives bearing vicinal tertiary and quaternary carbon stereocenters have been synthesized via light-induced N-heterocyclic carbene (NHC) catalyzed asymmetric [4 + 2] cycloaddition of 4-arylidenylpyrazolones and α-diazoketones in moderate to good yields with good enantio- and diastereoselectivities (24 examples, up to 93% yield, 95% ee and >20 : 1 dr). This protocol features mild reaction conditions, high efficiency, and broad substrate scope.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.