Synthesis of 1-amino-4-hydroxycyclohexane-1-carboxylic acids

  1. Avenoza, A. 1
  2. Cativiela, C. 2
  3. Fernández-Recio, M.A. 1
  4. Peregrina, J.M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

Zeitschrift:
Journal of the Chemical Society-Perkin Transactions n 1

ISSN: 0300-922X

Datum der Publikation: 1999

Ausgabe: 22

Seiten: 3375-3379

Art: Artikel

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DOI: 10.1039/A904132J SCOPUS: 2-s2.0-0002229020 WoS: WOS:000083844300021 GOOGLE SCHOLAR

Andere Publikationen in: Journal of the Chemical Society-Perkin Transactions n 1

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Zusammenfassung

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.