The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions
- Avenoza, A. 2
- Cativiela, C. 1
- París, M. 2
- Peregrina, J.M. 2
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1
Instituto de Nanociencia y Materiales de Aragón
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2
Universidad de La Rioja
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ISSN: 0040-4020
Año de publicación: 1996
Volumen: 52
Número: 13
Páginas: 4839-4848
Tipo: Artículo
beta Ver similares en nube de resultadosOtras publicaciones en: Tetrahedron
Resumen
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.