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Schurgers B.,Research Group of Organic Chemistry | Brigou B.,Vrije Universiteit Brussel | Urbanczyk-Lipkowska Z.,Polish Academy of Sciences | Tourwe D.,Research Group of Organic Chemistry | And 4 more authors.
Organic Letters | Year: 2014

Novel tricyclic tetrahydroazepinones were synthesized via an in situ Diels-Alder reaction of furan with cyclic allenamides. These reactive intermediates are the first examples of cyclic seven-membered allenamides and were prepared starting from N-(2-chloroallyl)-2-allylglycine derivatives via ring-closing metathesis followed by dehydrochlorination. The trapping of the intermediate cycloallene with furan occurred endo- and regioselectively and provided a convenient entry into new building blocks for medicinal chemistry. The diastereoselectivity of the cycloaddition was confirmed using quantum chemical computations. © 2014 American Chemical Society.

Marien N.,Research Group of Organic Chemistry | Brigou B.,Vrije Universiteit Brussel | Pinter B.,Vrije Universiteit Brussel | De Proft F.,Vrije Universiteit Brussel | Verniest G.,Research Group of Organic Chemistry
Organic Letters | Year: 2015

Novel spiropseudoindoxyls were synthesized in high yields via a fully regioselective Au(III)-catalyzed cycloisomerization of easily obtainable o-nitrophenylpropiolamides, followed by an intramolecular dipolar cycloaddition as key steps. This one-pot cascade reaction resulted in new tetracyclic pseudoindoxyls, which were hydrogenated toward the title compounds as single diastereomers via N-O cleavage. The mechanism of the gold catalyzed cycloisomerization was studied by DFT and suggests a reaction path without the intermediacy of gold carbenoid species in these cases. © 2014 American Chemical Society.

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