Aggregation‐Induced Asymmetric Synthesis of 2,3‐Dihydrobenzofurans by [4 + 1] Annulation with Substituted Salicyl N‐Phosphonyl Imines

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-06-18 DOI:10.1002/ejoc.202500426

Guigen Li, Qingkai Yuan, Jasmine Yan, Hao Liu, Destin Mununga Maleka, Eric Augusto Eichelmann, Olivia Villanueva, Anthony F. Cozzolino

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Abstract

The aggregation‐induced asymmetric synthesis of trans‐2,3‐dihydrobenzofuran compounds was achieved via the reaction of salicyl N‐phosphonyl imines with sulfur ylide. This transformation proceeds through a [4 + 1] annulation pathway, affording products in good to excellent yields with tunable diastereoselectivities. By employing various THF/EtOH cosolvent systems in conjunction with group‐assisted purification (GAP) chemistry, the conventional aggregation cosolvent systems were shown to play a crucial role in enhancing diastereoselectivity and modulating aggregate formation. This was supported by studies involving aggregation‐induced emission (AIE), aggregation‐induced polarization (AIP), and dynamic light scattering (DLS). The developed protocol provides a practical and versatile synthetic approach to 2,3‐dihydrobenzofuran scaffolds, highlighting the utility of aggregation‐induced asymmetric synthesis (AIAS) as a powerful strategy for achieving stereocontrol.

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[4 + 1]环化取代水杨基N -膦酰亚胺聚合诱导不对称合成2,3 -二氢苯并呋喃

通过水杨基N -膦酰亚胺与硫酰化反应，实现了聚集诱导的反式2,3 -二氢苯并呋喃化合物的不对称合成。这种转化通过[4 + 1]环化途径进行，提供具有可调非对选择性的良好至优异产量的产品。通过将各种THF/EtOH共溶剂体系与基团辅助净化（GAP）化学相结合，传统的聚集共溶剂体系在增强非对异选择性和调节聚集形成方面发挥了关键作用。这得到了聚集诱导发射（AIE）、聚集诱导极化（AIP）和动态光散射（DLS）研究的支持。该方案为2,3 -二氢苯并呋喃支架的合成提供了一种实用且通用的方法，突出了聚集诱导不对称合成（AIAS）作为实现立体控制的有力策略的实用性。

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.