Synthesis of methyl 2-exo-cyano-3-exo-phenyl-5,6-endo (or exo)-epoxybicyclo[2.2.1]heptane-2-endo-carboxylates in enantiomerically pure form
- Cativiela, C. 1
- Avenoza, A. 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: 0957-4166
Año de publicación: 1993
Volumen: 4
Número: 7
Páginas: 1677-1682
Tipo: Artículo
beta Ver similares en nube de resultadosOtras publicaciones en: Tetrahedron: Asymmetry
Resumen
The enantiomers (1R, 2R, 3S, 4S, 5S, 6S) and (1S, 2S, 3R, 4R, 5R, 6R) of the 2-exo-cyano-6-endo-hydroxy-5-exo-iodo-3-exo-phenylbicyclo[2.2.1]heptan e-2-endo-carboxylic acid lactone 4 and 5, obtained starting from the endo-cycloadducts of the asymmetric Diels-Alder reactions between cyclopentadiene and (E)-2-cyanocinnamates of (R)-pantolactone 2 and (S)-ethyl lactate 3, are converted into the methyl 2-exo-cyano-3-exo-phenyl-5,6-endo(and exo)-epoxybicyclo[2.2.1]heptane-2-endo-carboxylates 6, 7, 8 and 9 in enantiomerically pure form.