An approach to the synthesis and assignment of the absolute configuration of all enantiomers of ethyl hydroxy(phenyl)methane(P-phenyl)phosphinate |
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| Institution: | 1. Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland;2. Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50-383 Wrocław, Poland;1. Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019, USA;2. Department of Chemistry and Biochemistry, Trinity University, San Antonio, TX 78212, USA;3. CURRL, New Mexico State University, 945 College Dr., Las Cruces, NM 88003, USA;4. Department of Chemistry, University of Texas at El Paso, El Paso, TX 79968, USA;1. Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznań, Poland;2. National Institute of Medicines, Chełmska 30/34, 00-725 Warsaw, Poland;1. Organic Chemistry Department, Plaza de los Caídos 1-5, University of Salamanca, 37008 Salamanca, Spain;2. Industrial Chemistry and Environmental Engineering Department, Jose Gutierrez Abascal 2, Technical University of Madrid, 28006 Madrid, Spain;3. X-ray Diffraction Service, Plaza de los Caídos 1-5, University of Salamanca, 37008 Salamanca, Spain;1. Department of Chemistry, Colorado State University, Fort Collins, CO, United States;2. Department of Biochemistry & Molecular Biology, Colorado State University, Fort Collins, CO, United States |
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| Abstract: | Ethyl butyryloxy(phenyl)methane(P-phenyl)phosphinate was hydrolyzed using four bacterial species as biocatalysts. In all cases the reaction was stereoselective and isomers bearing an α-carbon atom with an (S)-configuration were hydrolyzed preferentially. Also a lack of stereoselectivity toward the phosphorus atom was observed. Hydrolysis of one enantiomeric mixture, namely mixture of (SP,R) and (RP,S) configuration afforded enantiomerically pure ethyl (RP,S)-hydroxy(phenyl)methane(P-phenyl)phosphinate, configuration of which was established by X-ray crystallography. The observed 1H and 31P NMR chemical shifts of Mosher esters of ethyl hydroxy(phenyl)methane(P-phenyl)phosphinate were correlated with the configurations of both stereogenic centers of all four stereoisomers. |
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