Marien Niels, Brigou Ben, Pinter Balazs, De Proft Frank, Verniest Guido
Research 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.
Org Lett. 2015 Jan 16;17(2):270-3. doi: 10.1021/ol503364w. Epub 2014 Dec 29.
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.
通过易于获得的邻硝基苯基丙炔酰胺的完全区域选择性金（III）催化的环异构化反应，以高产率合成了新型螺假吲哚酚，随后进行分子内偶极环加成反应作为关键步骤。这种一锅法串联反应生成了新的四环假吲哚酚，通过N-O键断裂将其氢化成单一非对映异构体的标题化合物。通过密度泛函理论（DFT）研究了金催化环异构化的机理，结果表明在这些情况下反应路径中不存在金卡宾物种中间体。
