Quantum Mechanical Predictions of the Stereoselectivities of Proline-Catalyzed Asymmetric Intermolecular Aldol Reactions

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 a...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2003-03, Vol.125 (9), p.2475-2479
Main Authors: Bahmanyar, S, Houk, K. N, Martin, Harry J, List, Benjamin
Format: Article
Language:English
Subjects:
Alcohols - chemical synthesis
Aldehydes - chemistry
Benzaldehydes - chemistry
Catalysis
Chemistry
Cyclohexanones - chemistry
Exact sciences and technology
Kinetics and mechanisms
Models, Molecular
Organic chemistry
Proline - chemistry
Quantum Theory
Reactivity and mechanisms
Stereoisomerism
Thermodynamics
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja028812d