Striking a Balance to Control Stereochemistry

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Science  30 Sep 2011:
Vol. 333, Issue 6051, pp. 1831-1832
DOI: 10.1126/science.1211195

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Xείρ, transliterated from Greek as “cheir” and translated as “hand,” is the origin of the word chiral (1). Chiral molecules come in pairs called enantiomers, and like a pair of hands, they are mirror images that cannot be superimposed on each other. Chemists often want to synthesize just one enantiomer of a molecule, especially for pharmaceutical applications. However, the design of catalysts that favor synthesis of one enantiomer over the other is often done with limited theoretical guidance. On page 1875 of this issue, Harper and Sigman (2) report a new approach to the quantitative prediction of how much of each enantiomer will be formed in an enantioselective reaction. Their approach refines some well-established methods for predicting how the rates of chemical reactions change when different substituents alter the shape or electronic properties of reactants.