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Synfacts 2010(4): 0399-0399
DOI: 10.1055/s-0029-1219506
DOI: 10.1055/s-0029-1219506
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed Synthesis of Pyrrolidines and Piperidines
J. Han, B. Xu*, G. B. Hammond*
University of Louisville, USA
Further Information
Publication History
Publication Date:
22 March 2010 (online)
Significance
Reported is the synthesis of pyrrolidines 3 and piperidines 6 via a copper-catalyzed, one-pot tandem hydroamination-alkynylation sequence. Microwave heating was found to be most efficient with an increase in the reaction time from 30 minutes to 12 hours observed when using conventional heating. A wide range of acetylenes 2 were tolerated, with excellent yields observed in all cases. The synthesis of fused product 7, obtained from a proline derivative, and one example of a seven-membered ring were also presented. An intermolecular variant, albeit in low yield, possibly heralds future synthetic opportunity.