期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 51, 页码 20690-20700出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja3086774
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Enantioselective gold-catalysis is emerging as a powerful tool in organic synthesis for the stereoselective manipulation of unfunctionalized unsaturated hydrocarbons. Despite the exponential growth, the molecular complexity of common chiral gold complexes generally prevents a complete description of the mechanism steps and activation modes being documented. In this study, we present the results of a combined experimental-computational (DFT) investigation of the mechanism of the enantioselective gold-catalyzed allylic alkylation of indoles with alcohols. A stepwise S(N)2 '-process (i.e. anti-auroindolination of the olefin, proton-transfer, and subsequent anti-elimination [Au]-OH) is disclosed, leading to a library of tricyclic-fused indole derivatives. The pivotal role played by the gold counterion, in terms of molecular arrangement (i.e. folding effect) and proton-shuttling in restoring the catalytic species, is finally documented.
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