Hydrosilylation of cinchonidine and 9-O-TMS-cinchonidine with triethoxysilane: application of 11-(triethoxysilyl)-10,11-dihydrocinchonidine as a chiral modifier in the enantioselective hydrogenation of 1-phenylpropane-1,2-dione

A1 Journal article (refereed)

Internal Authors/Editors

Publication Details

List of Authors: Lindholm A, Maki-Arvela P, Toukoniitty E, Pakkanen TA, Hirvi JT, Salmi T, Murzin DY, Sjoholm R, Leino R
Publication year: 2002
Journal: Journal of the Chemical Society, Perkin Transactions 1
Journal acronym: J CHEM SOC PERK T 1
Issue number: 23
Start page: 2605
End page: 2612
Number of pages: 8
ISSN: 1472-7781


The detailed synthesis and characterization of (-)-11-(triethoxysilyl)-10,11-dihydrocinchonidine (4), a starting material for the immobilization of (-)- cinchonidine on silica based supports, is described. Compound 4 together with its precursors 9-O-(trimethylsilyl)cinchonidine (2) and 9-O-(trimethylsilyl)-11-(triethoxysilyl)-10,11-dihydrocinchonidine (3) were employed as chiral modifiers in the hydrogenation of a prochiral diketone, 1-phenylpropane-1,2-dione, over a heterogeneous Pt/Al2O3 catalyst using cinchonidine (1) as a reference modifier. The unexpected enhancement of ee induced by 4, demonstrating the positive effect of distal modifier substitution, is discussed in the light of molecular modeling and NMR studies.

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