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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis of 2-spiropseudoindoxyls via an intramolecular nitroalkyne redox-dipolar cycloaddition cascade
Niels Marien1, Ben Brigou, Balazs Pinter
1Research Group of Organic Chemistry, Department of Chemistry and Department of Bio-Engineering Sciences, Faculty of Science and Bio-Engineering Sciences, and ‡Research Group of General Chemistry, Vrije Universiteit Brussel (VUB) , Pleinlaan 2, B-1050 Brussels, Belgium.
Abstract:
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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