Synthesis and dienophilic behavior of enantiomerically pure (E)-2-p-tolylsulfinylacrylonitrile derivatives

2002 
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.
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