Phosphine-Catalyzed Tandem Annulation/Rearrangement Reaction of Enynes with N-Tosylimines

IF 1.9 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Siting Qu, Shuang Gu, Yi Tang, Dr. Bing Zheng, Prof. Dr. Hongchao Guo
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Abstract

A phosphine-catalyzed tandem annulation/rearrangement reaction of yne-enones with N-tosylimines has been developed, which proceeds well to afford the conjugated imines in moderate to high yields as single geometric isomer. Under mild reaction conditions, this reaction shows good tolerance for a variety of yne-enones and N-tosylimines. This article provides 26 examples with yields up to 94% and diastereoselectivity greater than 20:1. The scale-up reaction and further transformations were also successful, making it a powerful tool for the synthesis of conjugated imine derivatives as single geometric isomers. In addition, a reasonable reaction mechanism involving [2 + 2] cycloaddition and rearrangement is proposed.

Abstract Image

膦催化烯类与n -托苯胺的串联环化/重排反应
本文研究了膦催化炔烯酮与n -甲苯胺的串联环化重排反应,得到了中高产率的共轭亚胺单几何异构体。在温和的反应条件下,该反应对多种炔烯酮和n -甲苯胺具有良好的耐受性。本文提供了26个产率高达94%,非对构选择性大于20:1的例子。放大反应和进一步的转化也很成功,使其成为合成共轭亚胺衍生物作为单一几何异构体的有力工具。提出了[2 + 2]环加成和重排的合理反应机理。
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来源期刊
ChemistrySelect
ChemistrySelect Chemistry-General Chemistry
CiteScore
3.30
自引率
4.80%
发文量
1809
审稿时长
1.6 months
期刊介绍: ChemistrySelect is the latest journal from ChemPubSoc Europe and Wiley-VCH. It offers researchers a quality society-owned journal in which to publish their work in all areas of chemistry. Manuscripts are evaluated by active researchers to ensure they add meaningfully to the scientific literature, and those accepted are processed quickly to ensure rapid online publication.
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