63743-97-5Relevant academic research and scientific papers
Highly efficient chiral polydentate sulfinyl ligands/catalysts containing prolinol moiety
Chrzanowski, Jacek,Rachwalski, Michal,Pieczonka, Adam M.,Leniak, Stanislaw,Drabowicz, Jzef,Kielbasiski, Piotr
, p. 2649 - 2655 (2016/05/10)
New polydentate chiral ligands, containing the hydroxyl group, stereogenic sulfinyl group and enantiomeric prolinol moieties were synthesized and proved very efficient catalysts in the asymmetric diethylzinc addition to benzaldehyde, the asymmetric aldol
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%.
