Abstract
Commonly observed, but often neglected, is the possibility of modifying the facial diastereoselectivity of nucleophilic addition to carbonyls by means of temperature and solvent. Temperature dependent measurements according to the modified Eyring equation allow the evaluation of stereoselectivity in terms of differential enthalpy and entropy contributions, and demonstrate the great importance of the entropic contribution in determining the facial diastereoselectivity. Even the reaction solvent proved to be important in directing the diastereoisomeric ratio. The inversion temperature (T inv ) that appears in non-linear Eyring plots mainly depends on the substrate solvation and corresponds to a transition between two differently ordered solvation states.KeywordsSolvent EffectInversion TemperatureNucleophilic AdditionDifferential EntropyTemperature Dependent MeasurementThese keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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