Addition of organolithium reagents to Ahc methyl ester. An approach to new alpha-amino ketones

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Peregrina, J.M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Tetrahedron

ISSN: 0040-4020

Año de publicación: 2002

Volumen: 58

Número: 51

Páginas: 10167-10171

Tipo: Artículo

DOI: 10.1016/S0040-4020(02)01363-7 SCOPUS: 2-s2.0-0037121778 WoS: WOS:000179789200009 GOOGLE SCHOLAR

Otras publicaciones en: Tetrahedron

Repositorio institucional: lock_openAcceso abierto Editor

Resumen

We have developed a versatile methodology to obtain α-amino ketones by acylation of methyl N-benzoyl-7-azabicyclo[2.2.1]heptane-1-carboxylate (1) with organolithium reagents. The reaction proceeds via a stable tetrahedral intermediate. When methyl ester 1 was treated under the same conditions but with a different work up procedure (careful addition of saturated NH4Cl), we observed by 1H NMR spectroscopy that a new compound had appeared in the crude reaction mixture corresponding to a hemiacetal. © 2002 Elsevier Science Ltd. All rights reserved.