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Synfacts 2009(4): 0370-0370  
DOI: 10.1055/s-0028-1087884
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Polysubstituted Pyrroles from (Z)-Enynols

Contributor(s): Victor Snieckus, Toni Rantanen
Y. Lu, X. Fu, H. Chen, X. Du, X. Jia, Y. Liu*
Shanghai Institute of Organic Chemistry and Shanghai University, P. R. of China
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Publication History

Publication Date:
23 March 2009 (online)

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Significance

An efficient one-pot synthesis of multisubstituted pyrroles is realized by the reaction of suitably substituted (Z)-enynols with tosyl amine and 4-nitrophenyl amine catalyzed by Au/Ag salts. Depending on the substitution pattern, the presence of the Lewis acid BF3˙Et2O was in some cases required to promote the first amination step. The reaction affords moderate to good yields, and substrate scope was reasonably well studied. The synthesis of the requisite (Z)-enynol starting materials was unfortunately not described.