Asymmetric Diels-Alder reactions of chiral (E)-2-cyanocinnamates with cyclopentadiene

  1. Cativiela, C. 2
  2. Mayoral, J.A. 2
  3. Avenoza, A. 1
  4. Peregrina, J.M. 1
  5. Lahoz, F.J. 2
  6. Gimeno, Sergio. 2
  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:
Journal of Organic Chemistry

ISSN: 0022-3263

Año de publicación: 1992

Volumen: 57

Número: 17

Páginas: 4664-4669

Tipo: Artículo

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DOI: 10.1021/JO00043A025 SCOPUS: 2-s2.0-0000521168 WoS: WOS:A1992JJ66800025 GOOGLE SCHOLAR

Otras publicaciones en: Journal of Organic Chemistry

Repositorio institucional: lock_openAcceso abierto Editor

Resumen

Several chiral derivatives of (E)-2-cyanocinnamic acid are used as trisubstituied dienophiles, and their asymmetric Diels-Alder reactions with cyclopentadiene are studied. The reactions of (E)-2-cyanocinnamates of (S)-ethyl lactate and (R)-pantolactone with cyclopentadiene, catalyzed by TiCl4, allow the synthesis of enantiomerically pure cycloadducts whose absolute configurations are assigned by an X-ray diffraction study of enantiomerically pure (1S,2S,3R,4R,5R,6R)-iodolactone. The results obtained show that the α-cyano group influences asymmetric induction, probably through an influence on the s-cis/s-trans equilibrium of the enoate moiety of the chiral dienophile. © 1992 American Chemical Society.