期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2012, 期 7, 页码 1336-1345出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101320
关键词
Asymmetric catalysis; Organo-catalysis; Alkaloids; Ketene dimeri-zation; Silicones; Supported catalysts
资金
- University of Pisa, Ministero dell'Universita e della Ricerca (MIUR)
- Consiglio Nazionale delle Ricerche - Istituto di Chimica dei Composti Organometallici (ICCOM-CNR)
A straightforward procedure is presented for the covalentimmobilization of ester and silyl ether derivatives of theCinchona alkaloid 10,11-dihydroquinidine within insoluble cross-linked silicone elastomeric films. These materials were effective heterogeneous organocatalysts in the asymmetric dimerization of ketenes, which provided chiral Weinreb beta-ketoamides in 2883?% yield and 7999?% ee in the course of several recycles. A productivity/enantioselectivity protocol is also proposed to better assess the relative merits of soluble and supported asymmetric catalytic systems towards process intensification.
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