The importance of entropy in stereoselection. Reduction of tert-butylcyclohexanone by lithium aluminum hydride

Article abstract of DOI:10.1016/0040-4039(96)00229-8

In the title reaction, the differences in both the enthalpy and the entropy of activation between the cis and trans diastereomers were measured (ΔΔH(≠) = -793 (56) cal/mol and ΔΔS(≠) = 2.00 (0.20) e.u.). The experimentally determined ΔΔH(≠) is shown to be