含n -酰基铵离子乙烯基重氮化合物的lewis酸催化非对映选择性[4 + 2]环加成

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-02-28 DOI:10.1021/acs.orglett.5c00581

Xiaofei Chen, Yihan Gao, Shuyu Yu, Jingyi Liang, Lei Zhou

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引用次数: 0

摘要

描述了由3-羟基异吲哚酮生成的乙烯基重氮化合物与n -酰基铵离子的fecl3催化[4 + 2]环加成反应。一系列含重氮的异吲哚[2,1- A]喹诺啉酮具有优异的非对映选择性，包括具有三个连续立体中心的化合物。根据剩余重氮官能团的丰富化学性质，产物很容易转化为各种异吲哚[2,1-a]喹诺啉酮衍生物。

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Lewis-Acid-Catalyzed Diastereoselective [4 + 2] Cycloaddition of Vinyldiazo Compounds with N-Acyliminium Cations

An FeCl₃-catalyzed [4 + 2] cycloaddition of vinyldiazo compounds with N-acyliminium cations generated from 3-hydroxyisoindolinones is described. A series of diazo-containing isoindolo[2,1-a]quinolinones were constructed in good yields with excellent diastereoselectivities, including those with three contiguous stereogenic centers. The resultant products were readily converted into various isoindolo[2,1-a]quinolinone derivatives based on the rich chemistry of the remaining diazo functionality.

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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.