A straightforward procedure is presented for the covalent immobilization of ester and silyl ether derivatives of the Cinchona 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.

Silicone-Supported Cinchona Alkaloid Derivatives as Insoluble Organocatalysts in the Enantioselective Dimerization of Ketenes

MANDOLI, ALESSANDRO
;
2012-01-01

Abstract

A straightforward procedure is presented for the covalent immobilization of ester and silyl ether derivatives of the Cinchona 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.
2012
Cancogni, D; Mandoli, Alessandro; Jumde, R; Pini, Dario
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/190456
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