| Abstract
| - The dienophilic behavior of the sulfilimine 2, synthesized from (Z)-3-p-tolylsulfinylacrylonitrile 1,in its Diels−Alder reactions with furan and acyclic dienes has been investigated. A complete π-facialselectivity for 2, opposite to that observed from its precursor 1, is the main feature of all thesecycloadditions. Moreover, the high exo selectivity observed in reactions of 2 with furan (not observedfor 1) contrasts with the almost complete endo selectivity with other cyclic and acyclic dienes.Additionally, the opposite regioselectivities obtained for 2 with Dane's diene and 1-substitutedbutadienes (not observed for 1) are also noteworthy. This behavior allows dienophiles 1 and 2 to beconsidered as complementary precursors from a synthetic point of view.
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