Divergent Construction of Spirocyclopentene-3,2′-indolines with Vicinal Stereocenters via Palladium-Catalyzed Aza-Wacker Cyclization

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-14 DOI:10.1021/acs.orglett.5c00931

Fan Yang, Huai-Yu Bin, Feng-Kai Zhao, Li Cheng, Hao Wang, Jian-Hua Xie

引用次数: 0

Abstract

Herein, we report an aerobic palladium-catalyzed aza-Wacker cyclization to produce spirocyclopentene-3,2′-indolines with vicinal stereocenters. Using 1,2-bis(diphenylphosphino)benzene (dppbz) and pyridine as ligands, we achieved a ligand-modulated diastereodivergent synthesis, producing cis- and trans-spirocyclopentene-3,2′-indolines with exceptional yields and diastereoselectivities. Density functional theory (DFT) calculations revealed that selective aza-Wacker cyclization proceeds through distinct trans- and cis-aminopalladation mechanisms.

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通过钯催化的 Aza-Wacker 环化反应异构出具有副立体中心的螺环戊烯-3,2′-吲哚类化合物

在这里，我们报道了一个有氧钯催化的aza-Wacker环化反应，以产生具有邻近立体中心的螺旋环戊烯-3,2 ' -吲哚。利用1,2-二（二苯基膦）苯（dppbz）和吡啶作为配体，我们实现了配体调制的非对映发散合成，生产了顺式和反式螺环戊烯-3,2 ' -吲哚，具有优异的产率和非对映选择性。密度泛函理论（DFT）计算表明，选择性aza-Wacker环化通过不同的反式和顺式氨基化机制进行。

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.