Determination of absolute configuration in 4-aryl-3, 4-dihydro-2(1H)-pyrimidones by high performance liquid chromatography and CD spectroscopy

W Krenn; P Verdino; G Uray; K Faber; C O Kappe

doi:10.1002/(SICI)1520-636X(1999)11:8<659::AID-CHIR8>3.0.CO;2-V

Determination of absolute configuration in 4-aryl-3, 4-dihydro-2(1H)-pyrimidones by high performance liquid chromatography and CD spectroscopy

Chirality. 1999;11(8):659-62. doi: 10.1002/(SICI)1520-636X(1999)11:8<659::AID-CHIR8>3.0.CO;2-V.

Authors

W Krenn¹, P Verdino, G Uray, K Faber, C O Kappe

Affiliation

¹ Institute of Organic Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, A-8010 Graz, Austria.

PMID: 10467318
DOI: 10.1002/(SICI)1520-636X(1999)11:8<659::AID-CHIR8>3.0.CO;2-V

Abstract

The absolute configuration of three 4-aryl-3, 4-dihydro-2(1H)-pyrimidones (Biginelli compounds, DHPMs) was established by comparison of the typical circular dichroism (CD) spectra of individual enantiomers with reference samples of known absolute configuration. The enantiomers were obtained by semipreparative separation of racemic mixtures on a Chiralcel OD-H chiral stationary phase. The method was used to establish the enantiopreference of various lipases in biocatalytic kinetic resolution experiments employing activated DHPM esters.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chromatography, High Pressure Liquid
Circular Dichroism
Pyrimidinones / chemistry*

Substances

Pyrimidinones