Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions.J Am Chem Soc. 2003 Jan 08; 125(1):16-7.JA
Abstract
Contrary to the widely accepted mechanism of the Hajos-Parrish-Eder-Sauer-Wiechert reaction, we have obtained evidence for the involvement of only one proline molecule in the transition states of both inter- and intramolecular aldol reactions. Our conclusions are based on kinetic measurements and the absence of nonlinear and dilution effects on the asymmetric catalysis, and are supported by B3LYP/6-31G* calculations. Complementary to recent theoretical studies, our results provide the foundation of a unified enamine catalysis mechanism of proline-catalyzed inter- and intramolecular aldol reactions.
Pub Type(s)
Journal Article
Research Support, U.S. Gov't, P.H.S.
Language
eng
PubMed ID
12515489
Citation
Hoang, Linh, et al. "Kinetic and Stereochemical Evidence for the Involvement of Only One Proline Molecule in the Transition States of Proline-catalyzed Intra- and Intermolecular Aldol Reactions." Journal of the American Chemical Society, vol. 125, no. 1, 2003, pp. 16-7.
Hoang L, Bahmanyar S, Houk KN, et al. Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions. J Am Chem Soc. 2003;125(1):16-7.
Hoang, L., Bahmanyar, S., Houk, K. N., & List, B. (2003). Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions. Journal of the American Chemical Society, 125(1), 16-7.
Hoang L, et al. Kinetic and Stereochemical Evidence for the Involvement of Only One Proline Molecule in the Transition States of Proline-catalyzed Intra- and Intermolecular Aldol Reactions. J Am Chem Soc. 2003 Jan 8;125(1):16-7. PubMed PMID: 12515489.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions.
AU - Hoang,Linh,
AU - Bahmanyar,S,
AU - Houk,K N,
AU - List,Benjamin,
PY - 2003/1/8/pubmed
PY - 2003/3/5/medline
PY - 2003/1/8/entrez
SP - 16
EP - 7
JF - Journal of the American Chemical Society
JO - J Am Chem Soc
VL - 125
IS - 1
N2 - Contrary to the widely accepted mechanism of the Hajos-Parrish-Eder-Sauer-Wiechert reaction, we have obtained evidence for the involvement of only one proline molecule in the transition states of both inter- and intramolecular aldol reactions. Our conclusions are based on kinetic measurements and the absence of nonlinear and dilution effects on the asymmetric catalysis, and are supported by B3LYP/6-31G* calculations. Complementary to recent theoretical studies, our results provide the foundation of a unified enamine catalysis mechanism of proline-catalyzed inter- and intramolecular aldol reactions.
SN - 0002-7863
UR - https://www.unboundmedicine.com/medline/citation/12515489/Kinetic_and_stereochemical_evidence_for_the_involvement_of_only_one_proline_molecule_in_the_transition_states_of_proline_catalyzed_intra__and_intermolecular_aldol_reactions_
DB - PRIME
DP - Unbound Medicine
ER -
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