TY - JOUR
T1 - Computational educidation of the catalytic mechanism for ketone reduction by an oxazaborolidine-borane adduct
AU - Linney, Lynda P.
AU - Self, Christopher R.
AU - Williams, Ian H.
PY - 1994/12/1
Y1 - 1994/12/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=37049079876&partnerID=8YFLogxK
U2 - 10.1039/C39940001651
DO - 10.1039/C39940001651
M3 - Article
AN - SCOPUS:37049079876
SN - 0022-4936
VL - 1994
SP - 1651
EP - 1652
JO - Journal of the Chemical Society, Chemical Communications
JF - Journal of the Chemical Society, Chemical Communications
IS - 14
ER -