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Synthesis 1997; 1997(2): 165-167
DOI: 10.1055/s-1997-1169
short paper
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Synthesis of exo-3-Hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylic Acid, a New Conformationally Constrained 4-Hydroxyproline

A. Avenoza1 , C. Cativiela2 , M. A. Fernández-Recio3 , J. M. Peregrina3
  • 1Department of Chemistry (Organic Chemistry). Edificio Científico-Técnico. Sección Ciencias. Universidad de La Rioja. 26001 Logroño, Spain, Fax +34(41)259431; E-mail alberto.avenoza@dq.unirioja.es
  • 2Department of Organic Chemistry. Instituto de Ciencia de Materiales de Aragón. Univesidad de Zaragoza-C.S.I.C. 50009 Zaragoza, Spain, Fax +34(76)761159; E-mail carlos.cativiela@msf.unizar.es
  • 3Department of Chemistry (Organic Chemistry). Edificio Científico-Técnico. Sección Ciencias. Universidad de La Rioja. 26001 Logroño, Spain
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Publication History

Publication Date:
31 December 2000 (online)

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A conformationally constrained α-amino-β-hydroxy bases upon 4-hydroxyproline has been prepared, starting from an iodooxazine intermediate, by opening of the heterocycle, further intramolecular nucleophilic displacement and subsequent hydrolysis.

iodo-1,3-oxazine intermediate - intramolecular nucleophilic displacement - 4-hydroxyproline - 7-azabicyclo[2.2.1]heptane skeleton