Journal
ACS ORGANIC & INORGANIC AU
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsorginorgau.3c00028
Keywords
gold carbenes; enynes; rearrangements; metal carbenes; cycloisomerization; DFT mechanisticstudy
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This study identifies the factors influencing the selectivity in single-cleavage skeletal rearrangements promoted by gold(I) catalysts. It is found that stereoconvergence is achieved through a rotational equilibrium when electron-rich substituents are utilized. The anomalous Z-selective skeletal rearrangement is primarily governed by electronic factors, while endo-selectivity relies on both steric and electronic factors.
We identify the factors that rule the selectivity insingle-cleavageskeletal rearrangements promoted by gold(I) catalysts. We find thatstereoconvergence is enabled by a rotational equilibrium when electron-richsubstituents are used. The anomalous Z-selectiveskeletal rearrangement is found to be due to electronic factors, whereas endo-selectivity depends on both steric and electronic factors.
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