Synthesis and dienophilic behavior of enantiomerically pure (E)-2-p-tolylsulfinylacrylonitrile derivatives
Por:
García Ruano J.L., González Gutiérrez L., Martín Castro A.M., Yuste F.
Publicada:
1 ene 2002
Resumen:
The synthesis of (E)-3-formyl 2-sulfinylacrylonitrile 2 and its diethylacetal derivative 3, as well as their behavior as dienophiles in reactions with cyclopentadiene are reported. The acetal 3 evolved with high ?-facial selectivity under Eu(fod)3 catalysis. The ?-facial selectivity became almost complete after extended reaction times, which evidences that a retro Diels-Alder reaction occurs. The endo/exo selectivity (ca. 80:20) was only moderate. The reactivity of the aldehyde 2 was higher but its evolution was less stereoselective than that of 3, the endo/exo product ratio observed being close to 1. © 2002 Elsevier Science Ltd. All rights reserved.
Filiaciones:
García Ruano J.L.:
Departamento de Química Orgánica (C-I), Facultad de Ciencias, 28049 Madrid, Spain
González Gutiérrez L.:
Departamento de Química Orgánica (C-I), Facultad de Ciencias, 28049 Madrid, Spain
Martín Castro A.M.:
Departamento de Química Orgánica (C-I), Facultad de Ciencias, 28049 Madrid, Spain
Yuste F.:
Departamento de Química Orgánica (C-I), Facultad de Ciencias, 28049 Madrid, Spain
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