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Quantum chemical calculations (B3LYP/6-31G(d)) on carbocation rearrangements that are proposed to occur in the biosynthesis of aspernomine are described. Based on these calculations, a pathway involving a concerted but asynchronous [4+2] cycloaddition that avoids the formation of a secondary carbocation is proposed for small model systems.
Quantum chemical calculations were used to characterize [4,5] sigmatropic shifts in systems containing butadiene and pentadienyl substructures. Cationic, anionic, and radical systems with various tethers connecting these substructures were examined. In many cases, concerted [4,5] sigmatropic shifts with asynchronous bond making and breaking events were observed. The fundamental connections between...
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