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Type: Artigo de periódico
Title: Electronically mediated selectivity in ring opening of 1-azirines. The 3-X mode: Convenient route to 3-oxazolines
Author: Sa, MCM
Kascheres, A
Abstract: The mild base-promoted reaction of methyl 2-phenyl-1-azirine-3-acetate (1) with aldehydes and acetone provides a new and simple route to the 3-oxazolines 5, which are formed in good yields by the electrophilic trapping of an imino anion produced by C-N bond cleavage in the 1-azirine enolate intermediate 6. Chloranil oxidation of 5 containing an aromatic substituent at C-2 affords oxazoles 7, while reaction of 5 containing an aliphatic group at C-2 produces 5-methylene-3-oxazolines 8 and 5-spiro-2-oxazolines 9 in addition to 7.
Editor: Amer Chemical Soc
Citation: Journal Of Organic Chemistry. Amer Chemical Soc, v. 61, n. 11, n. 3749, n. 3752, 1996.
Rights: fechado
Identifier DOI: 10.1021/jo9518866
Date Issue: 1996
Appears in Collections:Unicamp - Artigos e Outros Documentos

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