期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2015, 期 11, 页码 2503-2516出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500160
关键词
Organocatalysis; Aldol reactions; Kinetics; Reaction mechanisms; Transition states
资金
- Spanish Ministerio de Economia y Competitividad (MINECO)
- Fondo Europeo de Desarrollo Regional (FEDER) [CTQ2010-16959/BQU, CTQ2012-35535, CTQ2013-40855-R, CTQ2007-62771/BQU, CTQ2010-20387, CTQ2010-17436, CSD2007-00006]
- University of the Basque Country (UPV/EHU) [UFI11/22 QOSYC]
- Basque Government (GV/EJ) [IT-324-07]
- Generalitat Valenciana-FEDER [PROMETEO/2009/039]
- Gobierno de Aragon-FSE [E40]
- University of Alicante
- Donostia International Physics Center (DIPC)
- MINECO
The organocatalytic activities of highly substituted proline esters obtained through asymmetric [3+2] cycloadditions of azomethine ylides derived from glycine iminoesters have been analyzed by F-19 NMR and through kinetic isotope effects. Kinetic rate constants have been determined for unnatural proline esters incorporating different substituents. It has been found that exo-L and endo-L unnatural proline methyl esters yield opposite enantiomers in aldol reactions between cyclic ketones and aromatic aldehydes. The combined results reported in this study show subtle and remote effects that determine the organocatalytic behavior of these synthetic but readily available amino acid derivatives. These data can be used as design criteria for the development of new pyrrolidine-based organocatalysts.
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