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

A. Padwa; S. Lynch; J. Mejìa-Oneto; H. Zhang

doi:10.1055/s-2005-865368

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Synfacts 2005(0): 0017-0017
DOI: 10.1055/s-2005-865368

Synthesis of Heterocycles

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).