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Synfacts 2005(0): 0017-0017  
DOI: 10.1055/s-2005-865368
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Cycloaddition Chemistry of 2-Vinyl-Substi­-tuted Indoles and Related Heteroaromatics

Contributor(s): Victor Snieckus, Robert Engqvist
A. Padwa*, S. Lynch, J. Mejìa-Oneto, H. Zhang
Emory University, USA
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Publication History

Publication Date:
20 July 2005 (online)

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Significance

This report demonstrates the use of Rh(II)-catalyzed in situ generated push-pull dipoles in intramolecular 1,3-dipolar cycloadditions to derive pentacyclic frameworks in a stereocontrolled fashion. The push-pull dipoles are generated from readily prepared diazo 1,3-dicarbonyl compounds within several heteraromatic systems (indoles, benzofurans, furans and thiophenes).