Triflic Anhydride-Mediated Approach to Furo[3,2-<i>b</i>]furans from Diacetonide Protected Furanoses

Trifluoromethanesulfonic anhydride (Tf<sub>2</sub>O) exhibits excellent reactivity as an electrophile, serving as a highly versatile reagent in diverse chemical transformations. Herein, we report an operationally simple, efficient, unique, and practical one-step strategy for synthesizing diverse valuable structures bearing furo[3,2-<i>b</i>]furans core leveraging Tf<sub>2</sub>O's promoted reactivity of nitriles with diacetonide protected furanose. Furthermore, we demonstrate the potential of furo[3,2-<i>b</i>]furan as a precursor for complex structures through 1,3-dipolar cycloaddition.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-09-06
DOI
https://doi.org/10.1021/acs.joc.4c01067
Citations
3
Primary Topic
Advanced Synthetic Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.75

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article

Triflic Anhydride-Mediated Approach to Furo[3,2-b]furans from Diacetonide Protected Furanoses

Norein Sakander, Tariq Ahmad Dar, Qazi Naveed Ahmed, Mohammad Yaqoob Bhat
3 citations
The Journal of Organic Chemistry
Advanced Synthetic Organic Chemistry
0.75
article

Triflic Anhydride-Mediated Approach to Furo[3,2-b]furans from Diacetonide Protected Furanoses

Norein Sakander, Tariq Ahmad Dar, Qazi Naveed Ahmed, Mohammad Yaqoob Bhat
article en
3 citations

Abstract

Trifluoromethanesulfonic anhydride (Tf<sub>2</sub>O) exhibits excellent reactivity as an electrophile, serving as a highly versatile reagent in diverse chemical transformations. Herein, we report an operationally simple, efficient, unique, and practical one-step strategy for synthesizing diverse valuable structures bearing furo[3,2-<i>b</i>]furans core leveraging Tf<sub>2</sub>O's promoted reactivity of nitriles with diacetonide protected furanose. Furthermore, we demonstrate the potential of furo[3,2-<i>b</i>]furan as a precursor for complex structures through 1,3-dipolar cycloaddition.

The Journal of Organic ChemistryVol. 89(18)
Indian Institute of Integrative Medicine (IN), Academy of Scientific and Innovative Research (IN)
Science and Engineering Research Board
Openalex Percentile: Top 33%
Advanced Synthetic Organic Chemistry
0.75
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