Synthesis of enantiopure analogues of 3-hydroxyproline and derivatives

  1. Avenoza, A. 1
  2. Barriobero, J.I. 1
  3. Busto, J.H. 1
  4. Cativiela, C. 2
  5. 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

Revista:
Tetrahedron: Asymmetry

ISSN: 0957-4166

Año de publicación: 2002

Volumen: 13

Número: 6

Páginas: 625-632

Tipo: Artículo

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DOI: 10.1016/S0957-4166(02)00158-1 SCOPUS: 2-s2.0-0037134272 WoS: WOS:000175678200011 GOOGLE SCHOLAR

Otras publicaciones en: Tetrahedron: Asymmetry

Repositorio institucional: lock_openAcceso abierto Editor

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Resumen

All four enantiomerically pure 2-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylic acids, novel restricted analogues of 3-hydroxyproline, are described. The synthesis starts with the Diels-Alder reaction between methyl 2-benzamidoacrylate and Danishefsky's diene and uses as key steps a base-promoted internal nucleophilic displacement of the methanesulfonate group in the cyclohexane ring, followed by a resolution method that involves formation of diastereomers and further separation by crystallization. This synthetic route allowed us to obtain both enantiomers of the N-Boc-7-azabicyclo[2.2.1]heptan-2-ones, valuable ketones used as precursors of (-)- and (+)-epibatidine and other more interesting analogues. © 2002 Published by Elsevier Science Ltd.