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Synthesis 2016; 48(17): 2889-2895
DOI: 10.1055/s-0035-1561643
DOI: 10.1055/s-0035-1561643
paper
Sc(OTf)3-Catalyzed Cyclization of Allyl Amides of Ethenetricarboxylate
Further Information
Publication History
Received: 17 March 2016
Accepted after revision: 18 April 2016
Publication Date:
19 May 2016 (online)
Abstract
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.
Keywords
catalytic cyclization - Lewis acids - scandium triflate - ethenetricarboxylate - pyrrolidineSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561643. 1H and 13C NMR spectral data, and 2D NOESY spectra are included.
- Supporting Information
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For catalytic Friedel–Crafts acylation, see:
For catalytic substitution reactions of acetals, see:
For catalytic Prins-type reaction, see:
For recent examples of pyrrolidine syntheses, see: