Reactivity of (Z)-4-arylidene-5(4H)-oxazolones: [4+2] cycloaddition versus [4+3] cycloaddition/nucleophilic trapping

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Cativiela, C. 2
  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

Revista:
Tetrahedron Letters

ISSN: 0040-4039

Ano de publicación: 2002

Volume: 43

Número: 23

Páxinas: 4167-4170

Tipo: Artigo

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DOI: 10.1016/S0040-4039(02)00744-X SCOPUS: 2-s2.0-0037013823 WoS: WOS:000176083000011 GOOGLE SCHOLAR

Outras publicacións en: Tetrahedron Letters

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Resumo

The use of different aluminum derivatives in the reaction between cyclopentadiene and (Z)-2-phenyl-4-arylidene-5(4H)-oxazolones, and in particular the use of different equivalents of the reagent, allows the modulation of the synthesis of the norbornane skeleton by a [4+2] cycloaddition or the more interesting bicyclo[3.2.1]octane framework by a [4+3] cycloaddition followed by nucleophilic trapping of the ionic dipole cycloadduct with cyclopentadiene. © 2002 Elsevier Science Ltd. All rights reserved.