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Synfacts 2007(1): 0026-0026  
DOI: 10.1055/s-2006-955748
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Gold-Catalyzed Synthesis of Pyrrole-Fused Heterocycles

Contributor(s): Victor Snieckus, Wei Gan
I. V. Seregin, V. Gevorgyan*
University of Illinois at Chicago, USA
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Publikationsverlauf

Publikationsdatum:
15. Dezember 2006 (online)

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Significance

A reasonably efficient, gold-catalyzed synthesis of pyrroloheterocycles from TBS-propargylic alcohols of N-containing heterocycles is reported. The overall transformation involves alkyne-vinylidene isomerization with [1,2] migration of proton, silyl, stannyl and germyl groups followed by double [1,2]-hydride migration. The hydride shift component of the mechanism was verified by a D-labeling experiment. The scope of the method has not been sufficiently evaluated.