Stereoselective Tandem Cascade Furan Cycloadditions

Oligofurans linked by a rigid tether undergo tandem cycloaddition reactions with high stereoselectivity. The reaction of bisfurans with dimethyl acetylenedicarboxylate (DMAD) involves tandem [4 + 2]/[4 + 2] cycloadditions in a pincer mode. The reaction of oligofurans with arynes involves stereoselec...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-12, Vol.78 (24), p.12637-12649
Main Authors: Criado, Alejandro, Vilas-Varela, Manuel, Cobas, Agustín, Pérez, Dolores, Peña, Diego, Guitián, Enrique
Format: Article
Language:English
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Summary:Oligofurans linked by a rigid tether undergo tandem cycloaddition reactions with high stereoselectivity. The reaction of bisfurans with dimethyl acetylenedicarboxylate (DMAD) involves tandem [4 + 2]/[4 + 2] cycloadditions in a pincer mode. The reaction of oligofurans with arynes involves stereoselective tandem [4 + 2]/[4 + 2] cycloaddition reactions in a domino mode. The corresponding aryne adducts have been transformed into extended perylene derivatives by deoxygenation and aromatization with HCl/EtOH.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo4022265