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

A Lindholm, Päivi Mäki-Arvela, E Toukoniitty, TA Pakkanen, JT Hirvi, Tapio Salmi, Dmitry Murzin, R Sjoholm, Reko Leino

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Abstract

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.
Original languageUndefined/Unknown
Pages (from-to)2605–2612
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number23
DOIs
Publication statusPublished - 2002
MoE publication typeA1 Journal article-refereed

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