Triflic Anhydride-Mediated\nUnprecedented Reactivities\nof Diacetonide Endoglucofuranose and Ribose Tetracetate: Direct Access\nto γ‑Butenolides and Oxazoles

Herein, we present two unprecedented\nreactions for the\nsynthesis\nof γ-butenolides and oxazoles, leveraging Tf<sub>2</sub>O’s\npromoted reactivity of nitriles with diacetonide endoglucofuranose\nand 1,2,3,5-tetra-<i>O</i>-acetyl-β-d-ribofuranose.\nThis method is highly efficient and straightforward and employs a\none-step, metal-free protocol. It is effective with both aromatic\nand aliphatic nitriles and demonstrates a broad substrate scope. Our\napproach provides a versatile and practical pathway for the synthesis\nof structurally diverse compounds, significantly expanding the utility\nof Tf<sub>2</sub>O in synthetic chemistry.

Publication Details

Journal
Figshare
Published
2024-09-05
DOI
https://doi.org/10.1021/acs.joc.4c01423.s001
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
0.00
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article

Triflic Anhydride-Mediated\nUnprecedented Reactivities\nof Diacetonide Endoglucofuranose and Ribose Tetracetate: Direct Access\nto γ‑Butenolides and Oxazoles

Figshare
Cyclopropane Reaction Mechanisms
article

Triflic Anhydride-Mediated\nUnprecedented Reactivities\nof Diacetonide Endoglucofuranose and Ribose Tetracetate: Direct Access\nto γ‑Butenolides and Oxazoles

article en

Abstract

Herein, we present two unprecedented\nreactions for the\nsynthesis\nof γ-butenolides and oxazoles, leveraging Tf<sub>2</sub>O’s\npromoted reactivity of nitriles with diacetonide endoglucofuranose\nand 1,2,3,5-tetra-<i>O</i>-acetyl-β-d-ribofuranose.\nThis method is highly efficient and straightforward and employs a\none-step, metal-free protocol. It is effective with both aromatic\nand aliphatic nitriles and demonstrates a broad substrate scope. Our\napproach provides a versatile and practical pathway for the synthesis\nof structurally diverse compounds, significantly expanding the utility\nof Tf<sub>2</sub>O in synthetic chemistry.

Figshare
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Cyclopropane Reaction Mechanisms
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Triflic Anhydride-Mediated\nUnprecedented Reactivities\nof Diacetonide Endoglucofuranose and Ribose Tetracetate: Direct Access\nto γ‑Butenolides and Oxazoles · Figshare (2024) | TGRS Research Map | TGRS