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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
Cycloaddition Chemistry of 2-Vinyl-Substituted Indoles and Related Heteroaromatic Systems
J. Org. Chem.  2005,  70:  2206-2218  
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Publication History

Publication Date:
20 July 2005 (online)

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Key words

intramolecular cycloaddition - push-pull dipoles - indoles

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).

Comment

Cycloaddition reactions are efficient and stereoselective strategies for the construction of multifused ring systems. This contribution constitutes a systematic study which demonstrates the rapid assemblage, from easily constructed intermediates, of complex derivatives some of which are related to indole alkaloids.

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