Synthesis of Tetrasubstituted 2‐Pyrrolines via Zn(II)‐Catalyzed [3+2] Annulation of NH2‐Enaminones and N‐Tosylaziridines

IF 2.3 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2026-08-01 Epub Date: 2026-09-10 DOI:10.1002/ajoc.70520

Qingna Yang, Yan Xie, Liang Xie, Xinying Li, Ziyan Wu, Yucai Jiang, Huiyan Lou, Lulu Chen, Changyuan Zhang

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Abstract

A Zn(II)‐catalyzed [3+2] annulation of NH₂‐enaminones with N‐tosylaziridines is described. Various NH₂‐enaminones, along with diversely substituted N‐tosylaziridines, underwent this transformation to deliver tetrasubstituted 2‐pyrrolines in 44%–98% yields under mild conditions. This protocol offers broad substrate scope, good functional group tolerance, and high regioselectivity. Additionally, the resulting tetrasubstituted 2‐pyrrolines could be oxidized to pyrrole (under air/TFA) or undergo tosyl migration (under KOH), highlighting their synthetic versatility.

A Zn(II)‐catalyzed [3+2] annulation of NH₂‐enaminones with N‐tosylaziridines is developed, delivering tetrasubstituted 2‐pyrrolines in 44%–98% yields. This protocol represents a regioselective and versatile approach to tetrasubstituted 2‐pyrrolines, which can be further transformed into pyrroles or undergo tosyl migration, underscoring their synthetic utility.

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Zn（II）催化[3+2]环化nh2 -胺酮和n - tosylaziridine合成四取代2-吡咯啉

描述了Zn（II）催化nh2 -胺酮与n - tosyziridine的[3+2]环化反应。在温和的条件下，各种nh2 -胺酮以及不同取代的n - tosyziridine经过这种转化，以44%-98%的收率产生四取代的2-吡咯啉。该方案具有广泛的底物范围，良好的官能团耐受性和高区域选择性。此外，所得到的四取代2-吡咯可以被氧化成吡咯（在空气/TFA下）或进行tosyl迁移（在KOH下），突出了它们的合成通用性。

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.