可见光促进的三组分反应中吲哚的不对称c2功能化。

IF 3.8 2区化学 Q2 CHEMISTRY, APPLIED

Molecular Diversity Pub Date : 2025-08-15 DOI:10.1007/s11030-025-11319-y

Han-Peng Pan, Xiao-Ying Hu, Jun-Hui Luo, Zhao-Jie Fu, Xin-Yi Yao, Meng-Yan Ran, Fang-Xin Wang, Xiang-Zhi Zhang

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引用次数: 0

摘要

我们报道了一个可见光驱动的不对称三组分反应，使吲哚的直接对映选择性c2功能化。该方法利用芳基炔、苯醌和吲哚在手性磷酸催化下合成了含全碳季立体中心的手性吲哚衍生物。反应通过级联顺序进行：(1)Paternò-Büchi[2 + 2]芳炔和苯醌之间的环加成，(2)电环开环生成对醌的中间体，以及(3)在C2上对醌的1,6-吲哚的对映选择性加成。这种单烧瓶工艺锻造了三个具有高对映选择性的新键。重要的是，利用醛的功能，产品很容易转化为具有全碳四元立体中心的传统难以获得的吲哚，突出了该方法的合成实用性。

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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Asymmetric C2-functionalization of indoles via visible-light-promoted three-component reaction.

We report a visible-light-driven asymmetric three-component reaction enabling direct enantioselective C2-functionalization of indoles. This method utilizes arylalkynes, benzoquinones, and indoles under chiral phosphoric acid catalysis to construct chiral indole derivatives bearing all-carbon quaternary stereocenters. The reaction proceeds via a cascade sequence: (1) Paternò-Büchi [2 + 2] cycloaddition between arylalkynes and benzoquinones, (2) electrocyclic ring-opening to generate para-quinone methide intermediates, and (3) enantioselective 1,6-addition of indoles at C2 to the para-quinone methide. This single-flask process forges three new bonds with high enantioselectivity. Importantly, exploiting the aldehyde functionality, products are readily transformed into conventionally inaccessible indoles with all-carbon quaternary stereocenters, highlighting the synthetic utility of this methodology.

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来源期刊

Molecular Diversity 化学-化学综合

CiteScore

7.30

自引率

7.90%

发文量

219

审稿时长

2.7 months

期刊介绍： Molecular Diversity is a new publication forum for the rapid publication of refereed papers dedicated to describing the development, application and theory of molecular diversity and combinatorial chemistry in basic and applied research and drug discovery. The journal publishes both short and full papers, perspectives, news and reviews dealing with all aspects of the generation of molecular diversity, application of diversity for screening against alternative targets of all types (biological, biophysical, technological), analysis of results obtained and their application in various scientific disciplines/approaches including: combinatorial chemistry and parallel synthesis; small molecule libraries; microwave synthesis; flow synthesis; fluorous synthesis; diversity oriented synthesis (DOS); nanoreactors; click chemistry; multiplex technologies; fragment- and ligand-based design; structure/function/SAR; computational chemistry and molecular design; chemoinformatics; screening techniques and screening interfaces; analytical and purification methods; robotics, automation and miniaturization; targeted libraries; display libraries; peptides and peptoids; proteins; oligonucleotides; carbohydrates; natural diversity; new methods of library formulation and deconvolution; directed evolution, origin of life and recombination; search techniques, landscapes, random chemistry and more;