Computational educidation of the catalytic mechanism for ketone reduction by an oxazaborolidine–borane adduct
Abstract
The reaction pathway around the complete catalytic cycle for THF–borane reduction of propanone catalysed by the oxazaborolidine form (S)-proline has been determined by AM1 semiepirical MO calculations, including characterisation of all transition structures; the transition structure for ketone coordination is almost as high in energy as that for the rate-limiting hydride-transfer step, and the calculated kinetic isotope effect for reduction by THF–[2H3]borane is in accord with experiment.
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