Gold Catalysed 1,4-Enyne Acetate Strategy for the Synthesis of 1H-Indenes and Partially Hydrogenated Methanonaphtho[1,2-c]furan-1,3(4H)-diones

A synthetic method to prepare 1H-indenes and partially hydrogenated methanonaphtho[1,2-c]furan-1,3(4H)-diones from gold(I)-catalysed 1,4-enyne acetate cycloisomerisation and oxidation or Diels-Alder reaction with maleic anhydride is described. The proposed mechanism involves Rautenstrauch rearrangem...

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Published inAustralian journal of chemistry Vol. 73; no. 12; pp. 1165 - 1175
Main Authors Chen, Xiaoyu, Holm, Andrew Thomas, Chan, Philip Wai Hong
Format Journal Article
LanguageEnglish
Published CLAYTON Csiro Publishing 01.01.2020
CSIRO
Subjects
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Cyclic compounds
Decomposition
Diels-Alder reactions
Diketones
Experiments
Gold
Hydrogenation
Isomerization
Maleic anhydride
Oxidation
Physical Sciences
Science & Technology
Solvents
BRONSTED ACID
CYCLOADDITION
RAUTENSTRAUCH REARRANGEMENT
1,6-DIYNE CARBONATES
DIELS-ALDER REACTION
ESTERS
CYCLOISOMERIZATION
2-CYCLOPENTENONES
SELECTIVITY
CYCLIZATION
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Summary:A synthetic method to prepare 1H-indenes and partially hydrogenated methanonaphtho[1,2-c]furan-1,3(4H)-diones from gold(I)-catalysed 1,4-enyne acetate cycloisomerisation and oxidation or Diels-Alder reaction with maleic anhydride is described. The proposed mechanism involves Rautenstrauch rearrangement of the 1,4-enyne motif to give an in situ formed 1,3-cyclopentadiene intermediate. This is followed by 6-endo-dig cyclisation of the cyclic adduct and oxidation to give the aromatic carbocycle or Diels-Alder reaction with maleic anhydride to afford the bridged furan product.
ISSN:0004-9425
1529-5036
1445-0038
DOI:10.1071/CH20175