J. Ruano, Lorena González Gutiérrez, A. M. Castro
Sep 20, 2002
Citations
0
Influential Citations
9
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract 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 π-facial selectivity under Eu(fod)3 catalysis. The π-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.