The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions

  1. Avenoza, A. 2
  2. Cativiela, C. 1
  3. París, M. 2
  4. Peregrina, J.M. 2
  1. 1 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

  2. 2 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Aldizkaria:
Tetrahedron

ISSN: 0040-4020

Argitalpen urtea: 1996

Alea: 52

Zenbakia: 13

Orrialdeak: 4839-4848

Mota: Artikulua

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DOI: 10.1016/0040-4020(96)00155-X SCOPUS: 2-s2.0-0029989560 WoS: WOS:A1996UC44300024 GOOGLE SCHOLAR

Beste argitalpen batzuk: Tetrahedron

Gordailu instituzionala: lock_openSarbide irekia Editor

Garapen Iraunkorreko Helburuak

Laburpena

This report describes the behavior of four 1-amino-2-phenyl-1-cyclohexanecarboxylic acids, obtained in enantiomerically pure form starting from asymmetric Diels-Alder reactions between 1,3-butadiene and chiral (E)-2-cyanocinnamates, as chiral auxiliaries in the asymmetric Diels-Alder reactions of cyclopentadiene with chiral methyl N-acryloyl-1-amino-2-phenyl-1-cyclohexane-carboxylates. A model based on the formation of an intramolecular hydrogen bond accounts for the stereochemical outcome in the catalyzed reactions.