Diastereoselective Synthesis of Cyclobutanes via Rh-Catalyzed Unprecedented C–C Bond Cleavage of Alkylidenecyclopropanes

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-01-23 DOI:10.1021/acs.orglett.4c04779
Taeeun Kim, Taejoo Jeong, Eunjae Chung, Pargat Singh, Amitava Rakshit, Jihye Park, In Su Kim
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Abstract

The stereoselective synthesis of highly substituted cyclobutanes is essential for the development of lead candidates in drug discovery. Herein, we present a novel Rh(III)-catalyzed reaction pathway for synthesizing substituted cyclobutanes, which involves a concerted N–C bond formation and C–C bond cleavage between 2-aryl quinazolinones and alkylidenecyclopropanes. Notably, the combination of Rh(III) catalyst and HFIP solvent plays a critical role in facilitating the formation of cyclobutane rings.

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铑催化空前的烷基环丙烷C-C键裂解法合成环丁烷
高取代环丁烷的立体选择性合成是开发候选先导化合物的重要手段。本文提出了一种新的Rh(III)催化合成取代环丁烷的反应途径,该反应涉及2-芳基喹唑啉酮和烷基基环丙烷之间协调的N-C键形成和C-C键裂解。值得注意的是,Rh(III)催化剂和HFIP溶剂的结合对促进环丁烷环的形成起着至关重要的作用。
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来源期刊
Organic Letters
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.
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