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  Kinetic and Stereochemical Evidence for the Involvement of Only One Proline Molecule in the Transition States of Proline-Catalyzed Intra- and Intermolecular Aldol Reactions

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), 16-17. doi:10.1021/ja028634o.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0014-A4C9-3 Version Permalink: https://hdl.handle.net/21.11116/0000-0008-391C-A
Genre: Journal Article

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 Creators:
Hoang, Linh1, Author
Bahmanyar, S.2, Author
Houk, K. N.2, Author
List, Benjamin1, Author           
Affiliations:
1The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA., ou_persistent22              
2Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569 , ou_persistent22              

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 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.

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Language(s): eng - English
 Dates: 2002-09-202002-12-102003-01-01
 Publication Status: Issued
 Pages: 2
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/ja028634o
 Degree: -

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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 125 (1) Sequence Number: - Start / End Page: 16 - 17 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870