Phosphine-Catalyzed Asymmetric Dearomative [3+2] Annulation Reaction of Benzimidazoles with Cyclopropenones

IF 9.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

CCS Chemistry Pub Date : 2024-03-28 DOI:10.31635/ccschem.024.202403981

Shan-Shan Zhang, Rui-Xiang Wang, Qing Gu, Shu-Li You

引用次数: 0

Abstract

A phosphine-catalyzed intermolecular asymmetric dearomatization reaction of benzimidazoles with cyclopropenones has been developed. In the presence of 5 mol% of commercially available chiral phosphine catalyst, the dearomative [3+2] annulation reaction proceeds smoothly to afford the corresponding dearomatized heterocycles in excellent yields (up to 98%) and enantioselectivity (up to 99% ee). Meanwhile, this reaction features mild reaction conditions, excellent functional group tolerance, and the compatibility with gram-scale synthesis.

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磷催化的苯并咪唑与环丙烯酮的不对称[3+2]萃取反应

我们开发了一种膦催化的苯并咪唑与环丙烯酮的分子间不对称脱芳烃反应。在 5 mol% 的市售手性膦催化剂存在下，脱芳香[3+2]环化反应顺利进行，得到相应的脱芳香杂环，产率（高达 98%）和对映选择性（高达 99% ee）均非常好。同时，该反应具有反应条件温和、官能团耐受性好、可用于克级合成等特点。下载图表下载 PowerPoint

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来源期刊

CCS Chemistry Chemistry-General Chemistry

CiteScore

13.60

自引率

13.40%

发文量

475

审稿时长

10 weeks

期刊介绍： CCS Chemistry, the flagship publication of the Chinese Chemical Society, stands as a leading international chemistry journal based in China. With a commitment to global outreach in both contributions and readership, the journal operates on a fully Open Access model, eliminating subscription fees for contributing authors. Issued monthly, all articles are published online promptly upon reaching final publishable form. Additionally, authors have the option to expedite the posting process through Immediate Online Accepted Article posting, making a PDF of their accepted article available online upon journal acceptance.

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