Enzyme-promoted desymmetrization of bis(2-hydroxymethylphenyl) sulfoxide as a route to tridentate chiral catalysts |
| |
Authors: | Micha Rachwalski Magorzata Kwiatkowska Jzef Drabowicz Marcin Kos Wanda M Wieczorek Magorzata Szyrej Lesaw Siero Piotr Kiebasiski |
| |
Institution: | aCentre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, Sienkiewicza 112, 90-363 Łódź, Poland;bInstitute of General and Ecological Chemistry, Technical University of Łódź, Żeromskiego 116, 90-924 Łódź, Poland;cJan Długosz Academy, Institute of Chemistry and Environmental Protection, Armii, Krajowej 13/15, 42-201 Częstochowa, Poland |
| |
Abstract: | 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%. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|