DAST-Mediated Cyclization of α,α-Disubstituted-α-acylaminoketones: Efficient and Divergent Synthesis of Unprecedented Heterocycles

The design of a new potent nonsteroidal ecdysone agonist led to the discovery of a diethylaminosulfur trifluoride (DAST)-mediated cyclization of α,α-disubstituted-α-acylaminoketones. The resulting fluorooxazolines can be ring-opened or selectively substituted by a range of nucleophiles to provide in...

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Bibliographic Details
Published in:Organic letters 2011-01, Vol.13 (2), p.192-195
Main Authors: Bigot, Aurélien, Blythe, Judith, Pandya, Chirag, Wagner, Trixie, Loiseleur, Olivier
Format: Article
Language:English
Subjects:
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Diethylamines - chemistry
Fluorine - chemistry
Heterocyclic Compounds, 1-Ring - chemical synthesis
Heterocyclic Compounds, 1-Ring - chemistry
Ketones - chemistry
Molecular Structure
Oxazoles - chemical synthesis
Oxazoles - chemistry
Stereoisomerism
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Summary:The design of a new potent nonsteroidal ecdysone agonist led to the discovery of a diethylaminosulfur trifluoride (DAST)-mediated cyclization of α,α-disubstituted-α-acylaminoketones. The resulting fluorooxazolines can be ring-opened or selectively substituted by a range of nucleophiles to provide in high yields a diverse array of unprecedented heterocyclic frameworks.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102454e