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

Tutkimustuotos: LehtiartikkeliArtikkeliTieteellinenvertaisarvioitu

38 Sitaatiot (Scopus)

Abstrakti

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.
AlkuperäiskieliEi tiedossa
Sivut2605–2612
Sivumäärä8
JulkaisuJournal of the Chemical Society, Perkin Transactions 1
Numero23
DOI - pysyväislinkit
TilaJulkaistu - 2002
OKM-julkaisutyyppiA1 Julkaistu artikkeli, soviteltu

Viittausmuodot