Title

Metal-catalyzed cycloisomerization reactions of cis-4-hydroxy-5-alkynylpyrrolidinones and cis-5-hydroxy-6-alkynylpiperidinones: synthesis of Furo[3,2-b]pyrroles and Furo[3,2-b]pyridines

RIS ID

31111

Publication Details

Jury, J. C., Nalivela, K., Yazici, A., Willis, A. C. & Pyne, S. G. (2009). Metal-catalyzed cycloisomerization reactions of cis-4-hydroxy-5-alkynylpyrrolidinones and cis-5-hydroxy-6-alkynylpiperidinones: synthesis of Furo[3,2-b]pyrroles and Furo[3,2-b]pyridines. The Journal of Organic Chemistry, 74 (15), 5523-5527.

Abstract

Furo[3,2-b]pyrroles and furo[3,2-b]pyridines can be conveniently prepared in good yields from the cycloisomerization reactions of cis-4-hydroxy-5-alkynylpyrrolidinones and cis-5-hydroxy-6-alkynylpiperidinones, respectively, using Ag(I), Pd(II)/Cu(I), or Au(I) catalysis. In one case, the cycloisomerization product was unstable and produced a furan derivative by a ring-opening reaction.

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Link to publisher version (DOI)

http://dx.doi.org/10.1021/jo9007942