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

Forskningsoutput: TidskriftsbidragArtikelVetenskapligPeer review

37 Citeringar (Scopus)

Sammanfattning

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.
OriginalspråkOdefinierat/okänt
Sidor (från-till)2605–2612
Antal sidor8
TidskriftJournal of the Chemical Society, Perkin Transactions 1
Utgåva23
DOI
StatusPublicerad - 2002
MoE-publikationstypA1 Tidskriftsartikel-refererad

Citera det här