Jm. Coxon et al., FACTORS WHICH CONTROL PI-FACIAL SELECTION IN THE REDUCTION OF 5-SUBSTITUTED ADAMANTANONES, Journal of organic chemistry, 60(2), 1995, pp. 418-427
Ab initio and semiempirical calculations of the transition states for
reduction of 5-substituted adamantanones with AlH3 show bond lengtheni
ng and molecular orbitals consistent with hyperconjugative stabilizati
on. Electronic as well as torsional effects contribute to facial selec
tion.