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Density functional theory was used to locate transition states for hydroboration reactions of allenes with 9-borabicyclo[3.3.1]nonane and 10-R-9-borabicyclo[3.3.2]decane, as well as transition states for [1,3]-boratropic shift and aldehyde addition reactions of the derived allylboranes. The origin of kinetic versus thermodynamic control in the allene hydroboration step is described.

organic letters

Origin of Thermodynamic versus Kinetic Control of Allene Hydroboration with 9-Borabicyclo[3.3.1]nonane and 10(R)-Trimethylsilyl-9-Borabicyclo[3.3.2]decane