Interesting Behavior of α,β-Unsaturated Oximes in Intramolecular [4 + 2] Cycloaddition Reactions

Intramolecular [4 + 2] cycloaddition using α,β-unsaturated oximes was explored. The reactions proceeded under unusually facile conditions to furnish the nitrones. The latter were subsequently reacted with DMAD to afford [3 + 2] cycloaddition products.

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Bibliographic Details
Published in:Organic letters 2004-06, Vol.6 (12), p.1931-1934
Main Authors: François, David, Maden, Amy, Murray, William V
Format: Article
Language:English
Subjects:
Cyclization
Isoxazoles - chemical synthesis
Molecular Conformation
Nitrogen Oxides - chemistry
Oximes - chemical synthesis
Oximes - chemistry
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Summary:Intramolecular [4 + 2] cycloaddition using α,β-unsaturated oximes was explored. The reactions proceeded under unusually facile conditions to furnish the nitrones. The latter were subsequently reacted with DMAD to afford [3 + 2] cycloaddition products.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol049640n