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DOI: 10.1055/a-2702-1118
Aggregation-Induced Asymmetric Synthesis (AIAS) Leading to More Selective Formation of 2,3-Dihydrobenzofuran Based on Various Sulfur Ylides
Authors
Supported by: Welch Foundation D-1361-20210327
Funding Information We would like to acknowledge the financial support from Robert A. Welch Foundation (D-1361-20210327, USA) and the National Natural Science Foundation of China (Nos. 22071102 and 91956110).
Abstract
The 2,3-dihydrobenzofuran scaffold represents a key structural motif in many bioactive natural products and pharmaceutical compounds. Herein, we report an efficient [4 + 1] annulation of chiral salicyl N-phosphonyl imine with sulfur ylides under aggregation-induced conditions to access functionalized trans-2,3-dihydrobenzofuran derivatives. Systematic modulation of the THF/EtOH cosolvent ratios enable tunable diastereoselectivity, with diastereomeric ratios improving progressively as solvent polarity increased. Aggregation-induced emission (AIE), aggregation-induced polarization (AIP), and dynamic light scattering (DLS) analyses confirm the formation and evolution of chiral aggregates, providing mechanistic insight into the origin of aggregation-induced synthesis. Overall, this work highlights the application of aggregation-induced asymmetric synthesis (AIAS) to enhance stereocontrol and expand the synthetic toolbox for accessing functionalized 2,3-dihydrobenzofuran scaffolds.
Keywords
Aggregation-induced synthesis - Aggregation-induced emission - Aggregation-induced polarization - Dynamic light scattering - DihydrobenzofuransPublication History
Received: 08 July 2025
Accepted after revision: 15 September 2025
Accepted Manuscript online:
22 September 2025
Article published online:
23 October 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
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