Aggregation-Induced Asymmetric Synthesis (AIAS) Leading to More Selective Formation of 2,3-Dihydrobenzofuran Based on Various Sulfur Ylides

Qingkai Yuan; Jasmine X. Yan; Hao Liu; Patrick A. McDonough; Lina M. Delgado; Anthony F. Cozzolino; Dimitri Pappas; Kazimierz Surowiec; Guigen Li

doi:10.1055/a-2702-1118

Synthesis, Inhaltsverzeichnis

Synthesis
DOI: 10.1055/a-2702-1118

Paper

Aggregation-Induced Asymmetric Synthesis (AIAS) Leading to More Selective Formation of 2,3-Dihydrobenzofuran Based on Various Sulfur Ylides

Autoren

Qingkai Yuan‡
Jasmine X. Yan‡

¹Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, USA (Ringgold ID: RIN6177)
Hao Liu

¹Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, USA (Ringgold ID: RIN6177)
Patrick A. McDonough

¹Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, USA (Ringgold ID: RIN6177)
Lina M. Delgado

¹Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, USA (Ringgold ID: RIN6177)
Anthony F. Cozzolino

¹Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, USA (Ringgold ID: RIN6177)
Dimitri Pappas

¹Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, USA (Ringgold ID: RIN6177)
Kazimierz Surowiec

¹Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, USA (Ringgold ID: RIN6177)
Guigen Li

¹Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, USA (Ringgold ID: RIN6177)

Abstract

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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 - Dihydrobenzofurans

Volltext

Referenzen

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