Journal of the American Chemical Society 2003-03-05

Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions.

S Bahmanyar, K N Houk, Harry J Martin, Benjamin List

Index: J. Am. Chem. Soc. 125(9) , 2475-9, (2003)

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Abstract

Quantum mechanical calculations were employed to predict the ratio of four stereoisomeric products expected from two complex reactions involving the aldol reactions of cyclohexanone with benzaldehyde or with isobutyraldehyde catalyzed by (S)-proline. Experimental tests of these predictions provide an assessment of the state-of-the-art in quantum mechanical prediction of products of complex organic reactions in solution.