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- Title
Gold(I)-Catalyzed Generation of the Two Components of a Formal [4+2] Cycloaddition Reaction for the Synthesis of Tetracyclic Pyrano[2,3,4- de]chromenes.
- Authors
Arto, Tamara; Fañanás, Francisco J.; Rodríguez, Félix
- Abstract
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.
- Subjects
CALAVERITE; GOLD; CHEMICAL synthesis; PYRANONES; TRANSITION metals
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 25, p7334
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201602948