Synthesis of 1-amino-4-hydroxycyclohexane-1-carboxylic acids
- Avenoza, A. 1
- Cativiela, C. 2
- Fernández-Recio, M.A. 1
- Peregrina, J.M. 1
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1
Universidad de La Rioja
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2
Instituto de Nanociencia y Materiales de Aragón
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ISSN: 0300-922X
Ano de publicación: 1999
Volume: 22
Páxinas: 3375-3379
Tipo: Artigo
Outras publicacións en: Journal of the Chemical Society-Perkin Transactions n 1
Resumo
The synthesis of both stereoisomers of 1-amino-4-hydroxycyclohexane-1-carboxylic acid (1 and 2), a new family of constrained hydroxy-α,α-disubstituted-α-amino acids, is achieved through selective transformations of the functional groups of the corresponding enone cycloadduct provided by the Diels-Alder cycloadditipn of Danishefsky's diene to methyl 2-acetamidoacrylate. The stereochemistry of intermediates 8 and 9 in the synthesis of hydroxy-α-amino acids 1 and 2 was unambiguously confirmed by X-ray structure determination. ©The Royal Society of Chemistry 1999.