Construction of Chiral Spiro-Bridged Rings with Four Consecutive Stereocenters via Dearomative Diels-Alder Reactions of Anthracenes.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-14 DOI:10.1021/acs.orglett.5c01223

Gaofei Yang,Longqing Yang,Zhenzhong Liu,Yilun Song,Yinhe Qu,Shunxi Dong,Xiaoming Feng

引用次数: 0

Abstract

A highly diastereo- and enantioselective dearomative Diels-Alder reaction was accomplished by chiral N,N'-dioxide/Mg(II) complex catalyst. Various anthracene derivatives and methyleneindolinones efficiently transformed into the corresponding chiral spiro-bridged cyclic products with four consecutive stereocenters in good yields, excellent dr and er values under mild conditions (46 examples, up to 99% yield, >19:1 dr, >99:1 er). Gram-scale synthesis of chiral products and their further transformations were feasible. On the basis of theoretical calculation, possible working modes were provided to understand the origin of stereoselectivity of this transformation.

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蒽酮脱芳双醛-阿尔德反应构建具有四个连续立体中心的手性螺桥环。

采用手性N，N'-二氧化氮/Mg（II）络合催化剂，实现了高度非映对和对映选择性的Diels-Alder脱芳反应。在温和条件下，各种蒽衍生物和亚甲基吲哚酮能高效转化为相应的具有四个连续立体中心的手性螺桥环产物，产率高，dr和er值优异（46例，产率高达99%，>19:1 dr, >99:1 er）。手性产物的克级合成及其进一步转化是可行的。在理论计算的基础上，提供了可能的工作模式，以了解这种转变的立体选择性的来源。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.