Abstract
Abstract In an effort to test the applicability of the semi-empirical model for asymmetric induction5 to reactions of α-hydroxycarbonyl compounds, we monitored the diastereomeric ratio of diols obtained from the reactions of R-α-hydroxypropionaldehyde with LAH, MeLi and PhLi as a function of temperature and reagent concentration. In all these reactions the predominant diastereomer had the RR-configuration. However, whereas the diastereomeric product ratio of the first two reactions was enthalpy controlled, i.e. enthalpy favored the “correct” or predominant diastereomer, that of the reaction involving PhLi favored the “incorrect”, or minor diastereomer. In this reaction the diastereomeric ratio was entropy controlled. The usefulness and limitations of this model are discussed.
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