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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: Sá, Marcus C. M.
Kascheres, Albert
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.
Rights: fechado
Identifier DOI: 
Date Issue: 1996
Appears in Collections:Unicamp - Artigos e Outros Documentos

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