Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 25, Pages 7218-7221Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201602948
Keywords
cascade reactions; cycloaddition; gold; homogeneous catalysis; synthetic methods
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Funding
- MINECO-Spain [CTQ2013-41336-P]
- FICYT of Principado de Asturias (Severo Ochoa predoctoral grant)
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Ortho-Alkynylbenzaldehydes have been widely used to generate isochromenylium derivatives through gold-catalyzed cycloisomerization. These isochromenylium derivatives have been exploited as formal diene derivatives for reactions with different dienophiles. Herein, we describe the behavior of ortho-alkynylsalicylaldehydes, a particular case of ortho-alkynylbenzaldehydes. The gold-catalyzed cycloisomerization of ortho-alkynylsalicylaldehydes delivers an unusual heterodiene derivative that reacts with electron-rich alkenes through a formal [4+2] cycloaddition. In this reaction, both the diene and dienophile are generated in situ through gold-catalyzed cycloisomerization of appropriate alkynamines or alkynols. This reaction was used to synthesize complex tetracyclic pyrano[2,3,4-de]chromenes from two very simple starting materials (an ortho-alkynylsalicylaldehyde and an alkynamine or alkynol) with complete atom economy and with selective formation of bonds, cycles, and stereocenters.
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