Sc(OTf)3-Catalyzed Cyclization of Allyl Amides of Ethenetricarboxylate.

Catalytic cyclization of allyl amides of ethenetricarboxylate leading to pyrrolidines has been examined. Reaction of allyl amides of ethenetricarboxylate with Sc(OTf)₃ (0.2 equiv) gave 4-hydroxymethyl- 2-oxopyrrolidine derivatives as major products. The formation of hydroxymethylpyrrolidines may arise from participation of adventitious water in situ. Sc(OTf)₃-catalyzed cyclization reactions of the allyl amides with TMSX (X = Cl, Br) proceeded efficiently to give halogenated 2-oxopyrrolidine derivatives. Sc(OTf)₃-catalyzed cyclization reactions of the allyl ester with TMSX (X= Cl, Br) also proceeded to give halogenated 2- oxotetrahydrofuran derivatives. [ABSTRACT FROM AUTHOR]