Computational educidation of the catalytic mechanism for ketone reduction by an oxazaborolidine–borane adduct
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 14,p. 1651-1652
- https://doi.org/10.1039/c39940001651
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.Keywords
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