168140-89-4Relevant academic research and scientific papers
Highly stereoselective palladium-catalyzed coupling reactions of captodative olefins acetylvinyl arenecarboxylates
Villar, Lourdes,Bullock, Joseph P.,Khan, Matheen M.,Nagarajan, Arumugam,Bates, Roderick W.,Bott, Simon G.,Zepeda, Gerardo,Delgado, Francisco,Tamariz, Joaquin
, p. 9 - 17 (1996)
The palladium-catalyzed reaction of the captodative olefin 3-(p-nitrobenzoyloxy)-3-buten-2-one (1a) with aryl and vinyl halides gave coupled products 4-aryl-and 4-vinyl-3-(p-nitrobenzoyloxy)-3-buten-2-ones, 4 and 6 respectively, with high Z stereoselectio
Stereoselective synthesis, NMR conformational study and Diels-Alder reaction of β-functionalized 1-acetylvinyl arenecarboxylates
Peralta, Javier,Bullock, Joseph P.,Bates, Roderick W.,Bott, Simon,Zepeda, Gerardo,Tamariz, Joaquin
, p. 3979 - 3996 (1995)
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.
