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Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions.
J Am Chem Soc. 2003 Mar 05; 125(9):2475-9.JA

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.

Authors+Show Affiliations

Bahmanyar S
Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569, USA.
Houk KN
No affiliation info available
Martin HJ
No affiliation info available
List B
No affiliation info available

MeSH

AlcoholsAldehydesBenzaldehydesCatalysisCyclohexanonesModels, MolecularProlineQuantum TheoryStereoisomerismThermodynamics

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

12603135

Citation

Bahmanyar, S, et al. "Quantum Mechanical Predictions of the Stereoselectivities of Proline-catalyzed Asymmetric Intermolecular Aldol Reactions." Journal of the American Chemical Society, vol. 125, no. 9, 2003, pp. 2475-9.
Bahmanyar S, Houk KN, Martin HJ, et al. Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions. J Am Chem Soc. 2003;125(9):2475-9.
Bahmanyar, S., Houk, K. N., Martin, H. J., & List, B. (2003). Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions. Journal of the American Chemical Society, 125(9), 2475-9.
Bahmanyar S, et al. Quantum Mechanical Predictions of the Stereoselectivities of Proline-catalyzed Asymmetric Intermolecular Aldol Reactions. J Am Chem Soc. 2003 Mar 5;125(9):2475-9. PubMed PMID: 12603135.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions. AU - Bahmanyar,S, AU - Houk,K N, AU - Martin,Harry J, AU - List,Benjamin, PY - 2003/2/27/pubmed PY - 2003/5/7/medline PY - 2003/2/27/entrez SP - 2475 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 125 IS - 9 N2 - 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. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/12603135/Quantum_mechanical_predictions_of_the_stereoselectivities_of_proline_catalyzed_asymmetric_intermolecular_aldol_reactions_ DB - PRIME DP - Unbound Medicine ER -