5-Alkoxyoxazole - A Versatile Building Block in (Bio)organic Synthesis

The 5‐alkoxyoxazole ring system has proved to be a useful and versatile building block that is involved in a variety of chemical transformations (e.g., hetero‐Diels–Alder reactions, formal 1,3‐dipolar cycloadditions, photochemical [2+2] cycloadditions, Claisen rearrangements, and ring‐opening proces...

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Bibliographic Details
Published in:European journal of organic chemistry 2016-07, Vol.2016 (20), p.3264-3281
Main Authors: Jouanno, Laurie-Anne, Renault, Kévin, Sabot, Cyrille, Renard, Pierre-Yves
Format: Article
Language:English
Subjects:
Chemical Sciences
Cycladdition
Nitrogen heterocycles
Oxygen heterocycles
Sigmatropic rearrangment
Total synthesis
Ylides
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Summary:The 5‐alkoxyoxazole ring system has proved to be a useful and versatile building block that is involved in a variety of chemical transformations (e.g., hetero‐Diels–Alder reactions, formal 1,3‐dipolar cycloadditions, photochemical [2+2] cycloadditions, Claisen rearrangements, and ring‐opening processes). 5‐Alkoxyoxazoles have provided synthetic access to heteroaromatic scaffolds such as pyridines, furans, oxadiazolines, pyrrolidines, and significant linear chemical patterns, including amino acid derivatives. This review focuses on the broad range of reactivity of 5‐alkoxyoxazoles and their subsequent applications to the syntheses of naturally occurring compounds and biologically active molecules. 5‐Alkoxyoxazoles are versatile building blocks that can be employed in many chemical transformations, such as hetero‐Diels–Alder reactions, formal 1,3‐dipolar cycloadditions, photochemical [2+2] cycloadditions, rearrangements, and ring‐opening processes. We have focused on the reactivity of 5‐alkoxyoxazoles and their use in the syntheses of natural products and biologically active molecules.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600127