期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2013, 期 28, 页码 6254-6258出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301041
关键词
Organocatalysis; Aldol reactions; Asymmetric catalysis; Biphasic catalysis; Immobilization; Perfluorinated solvents
资金
- Ministerio de Econom a y Competitividad (MINECO) [CTQ2008-00947/BQU, CTQ2012-38594-C02-01]
- Departament d'Economia i Coneixement (DEC) [2009SGR623]
- ICIQ Foundation
- Ministerio de Ciencia e Innovacion (MICINN)
A polyfluoroalkyl derivative of 4-hydroxyproline, assembled through a 1,2,3-triazole linker (i.e., 7), displays high catalytic activity and enantioselectivity in aldol reactions of acetone with aromatic aldehydes featuring electron-withdrawing groups. The scope of the reaction with respect to the aldehyde acceptor can be expanded with the use of a bifunctional urea cocatalyst. The presence of the fluorous tag allows the aldol reactions to be performed in a perfluorohexane/acetone biphasic system. In this way, both the catalyst and the perfluorinated solvent can be easily recycled and reused (>6 times). In addition, the combination of the fluorous tag, triazole linker, and catalytic proline unit confers unprecedented substrate specificity for acetone upon 7.
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