Journal
ORGANIC LETTERS
Volume 17, Issue 2, Pages 270-273Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol503364w
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- Vrije Universiteit Brussel
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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.
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