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 β-ketoamides in 28-83 % yield and 79-99 % 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. A series of hydroquinidine derivatives embedded into elastomeric silicone films was prepared and used as insoluble organocatalysts in the asymmetric dimerization of ketenes. A protocol was introduced to compare the productivity/ enantioselectivity of the supported catalysts with those of their analogous soluble counterparts.

Silicone-supported Cinchona alkaloid derivatives as insoluble organocatalysts in the enantioselective dimerization of ketenes / D. Cancogni, A. Mandoli, R.P. Jumde, D. Pini. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2012:7(2012 Jan 25), pp. 1336-1345. [10.1002/ejoc.201101320]

Silicone-supported Cinchona alkaloid derivatives as insoluble organocatalysts in the enantioselective dimerization of ketenes

D. Cancogni;
2012

Abstract

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 β-ketoamides in 28-83 % yield and 79-99 % 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. A series of hydroquinidine derivatives embedded into elastomeric silicone films was prepared and used as insoluble organocatalysts in the asymmetric dimerization of ketenes. A protocol was introduced to compare the productivity/ enantioselectivity of the supported catalysts with those of their analogous soluble counterparts.
Alkaloids; Asymmetric catalysis; Ketene dimerization; Organocatalysis; Silicones; Supported catalysts; Organic Chemistry; Physical and Theoretical Chemistry
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/247748
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