1082072-40-9Relevant academic research and scientific papers
Highly enantioselective Henry reaction catalyzed by chiral tridentate heteroorganic ligands
Rachwalski, Michal,Lesniak, Stanislaw,Sznajder, Ewelina,Kielbasinski, Piotr
, p. 1547 - 1549 (2009)
New tridentate enantiomerically pure heteroatom catalysts, containing hydroxyl, sulfinyl and amino groups, proved to be highly efficient in the enantioselective nitroaldol (Henry) reaction to give the desired adducts in very high yields (up to 90%) and wi
Efficient catalysts for asymmetric Mannich reactions
Rachwalski, Micha?,Leenders, Tim,Kaczmarczyk, Sylwia,Kie?basiński, Piotr,Le?niak, Stanis?aw,Rutjes, Floris P. J. T.
, p. 4207 - 4213 (2013/07/11)
Efficient chiral catalysts for direct asymmetric three-component Mannich reactions of ketones, aldehydes and an amine (p-anisidine) have been developed. The corresponding β-amino carbonyl compounds (Mannich adducts) were obtained in good chemical yields a
Enzyme-promoted desymmetrization of bis(2-hydroxymethylphenyl) sulfoxide as a route to tridentate chiral catalysts
Rachwalski, Michal,Kwiatkowska, Malgorzata,Drabowicz, Jozef,Klos, Marcin,Wieczorek, Wanda M.,Szyrej, Malgorzata,Sieron, Leslaw,Kielbasinski, Piotr
, p. 2096 - 2101 (2008/12/22)
The desymmetrization of prochiral bis(2-hydroxymethylphenyl) sulfoxide 3 was efficiently performed via acetylation promoted by commonly available lipases. Two lipases, namely, CAL-B and LPL proved particularly efficient to give 2-acetoxymethylphenyl 2-hydroxymethylphenyl sulfoxide 4 in up to 98% yield and with up to 98% ee. On the basis of an X-ray analysis, the absolute configuration of 4 was determined as (+)-(R). The enantiomerically pure product 4 was then transformed into a series of enantiomerically pure diastereomeric 2-aminomethylphenyl 2-hydroxymethylphenyl sulfoxides 8 in which the amino groups originated from enantiomerically pure amines having additional C-stereogenic centres. Compounds 8 were examined as possible tridentate chiral catalysts in a reference reaction of diethylzinc with benzaldehyde to give the expected product, 1-phenylpropan-1-ol, in moderate yields and with ee's of up to 50%.
