Stereoselective and Regioselective Synthesis of Chiral Dihydrofurocoumarins as Glycohybrids

Herein, we report a new single-step process for the synthesis of chirally pure dihydrofurocoumarins, demonstrating high regio- and stereoselectivity. This method involves a diverse range of 4-hydroxy coumarin derivatives, which react with various d-glycals in the presence of ceric ammonium nitrate (CAN) at 90 °C to furnish dihydrofurocoumarins within 1 h in a good isolated yield. This developed method possesses several advantages such as its quick reaction time, wide substrate scope, and generation of two new chiral centers along with the inherited chirality of d-glycals, in the final products, enhancing their possible potential applications in medicinal chemistry, material science, and chemical biology.

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Publication Details

Journal
Organic Letters
Published
2025-10-28
DOI
https://doi.org/10.1021/acs.orglett.5c03991
Citations
1
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
0.94
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article

Stereoselective and Regioselective Synthesis of Chiral Dihydrofurocoumarins as Glycohybrids

Priti Kumari, Ram Sagar, Ghanshyam Tiwari, Chintam Narayana
1 citations
Organic Letters
Carbohydrate Chemistry and Synthesis
0.94
article

Stereoselective and Regioselective Synthesis of Chiral Dihydrofurocoumarins as Glycohybrids

Priti Kumari, Ram Sagar, Ghanshyam Tiwari, Chintam Narayana
article en
1 citations

Abstract

Herein, we report a new single-step process for the synthesis of chirally pure dihydrofurocoumarins, demonstrating high regio- and stereoselectivity. This method involves a diverse range of 4-hydroxy coumarin derivatives, which react with various d-glycals in the presence of ceric ammonium nitrate (CAN) at 90 °C to furnish dihydrofurocoumarins within 1 h in a good isolated yield. This developed method possesses several advantages such as its quick reaction time, wide substrate scope, and generation of two new chiral centers along with the inherited chirality of d-glycals, in the final products, enhancing their possible potential applications in medicinal chemistry, material science, and chemical biology.

Organic LettersVol. 27(44)
Jawaharlal Nehru University (IN), Physical Sciences (United States) (US)
Openalex Percentile: Top 20%
Carbohydrate Chemistry and Synthesis
0.94
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