Resumen
A stereoselective synthesis of novel β-substituted 1-acetylvinyl arenecarboxylates 2a-2h, via the bromo derivative 4a, is described. Isomer Z was the only product formed. Low temperature NMR experiments showed an s-cis/s-trans (20:80) conformeric equilibrium, and also a restricted rotational C-N barrier in 2a. X-ray diffraction of the latter revealed a planar s-trans conformation. Alkene 4a proved to be more reactive than 2a-2h towards cyclopentadiene (6) and isoprene (11) in Diels-Alder additions, giving the corresponding adducts 10 and 14 in high stereo- and regioselectivity.
Idioma original | Inglés |
---|---|
Páginas (desde-hasta) | 3979-3996 |
Número de páginas | 18 |
Publicación | Tetrahedron |
Volumen | 51 |
N.º | 14 |
DOI | |
Estado | Publicada - 3 abr. 1995 |