Utilize este identificador para referenciar este registo:
https://hdl.handle.net/1822/72916
Título: | Synthesis and reactivity of beta-bromo-beta-substituted dehydroalanines |
Autor(es): | Ferreira, Paula M. T. Monteiro, Luís S. |
Palavras-chave: | Nonproteinogenic amino acids Alanine derivatives Glycine derivatives |
Data: | Jul-2006 |
Editora: | Wiley-VCH Verlag |
Revista: | European Journal of Organic Chemistry |
Resumo(s): | The methyl ester of N-tert-butoxycarbonyl-(Z)-beta-bromo-beta-(1,2,4-triazol-1-yl)dehydroalanine was prepared by treatment of the methyl ester of N-tert-butoxycarbonyl-(E)-beta-(1,2,4-triazol-1-yl)dehydroalanine with N-bromosuccinimide (NBS), followed by Et3N. The reactivities of this compound and of our previously synthesized methyl ester of N-tert-butoxycarbonyl-beta,beta-dibromodehydroalanine towards several nucleophiles were studied, and it was found that these compounds react with oxygen nucleophiles to give the corresponding alpha-alkoxy-beta,beta-disubstituted alanines. Addition to the a-carbon atom also occurred when the beta,beta-dibromodehydroalanine derivative was treated with primary amines, giving alpha-amino-beta,beta-dibromoalanines. Treatment of the beta-bromo-beta-(1,2,4-triazol-1-yl)dehydroalanine derivative with amines gave alpha-(alkylamino)-beta-(alkylimino)alanines in high yields. These iminoalanines afforded alpha-aminoglycines when treated with silica in dichloromethane. (c) Wiley-VCH Verlag GmbH & Co. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/72916 |
DOI: | 10.1002/ejoc.200600094 |
ISSN: | 1434-193X |
Versão da editora: | https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.200600094 |
Arbitragem científica: | yes |
Acesso: | Acesso aberto |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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2006-Eur. J. Org. Chem. 3226.pdf | 177,85 kB | Adobe PDF | Ver/Abrir |