An approach to the synthesis and assignment of the absolute configuration of all enantiomers of ethyl hydroxy(phenyl)methane(P-phenyl)phosphinate

Effective fungal catalyzed synthesis of P-chiral organophosphorus compounds

“…The racemic mixture consisted of four stereoisomers: a left pair (R p R),(S p S) and a right one (R p S),(S p R). 15 Isolated enantiomers of the above-mentioned compounds are very attractive for further application as chiral building blocks in chemoenzymatic synthesis. Some effort has already been undertaken to separate all the enantiomeric forms of ethyl hydroxy(phenyl)methane(P-phenyl)phosphinate 15 but the results, based on the lipase activity, showed it to be unsuccessful.…”

“…These results allowed us to separate the obtained diastereoisomeric mixture using common column chromatography techniques. 15 The next step included the determination of the absolute configuration of the unreacted stereoisomers of ethyl hydroxy(phenyl)methane(P-phenyl)phosphinate. Usually NMR spectra are used as a tool for the determination of the absolute configuration of hydroxyphosphonates and hydroxyphosphinates, 8,17 mainly because of the simple method of sample preparation and because small amounts of the examined compound are required.…”

“…The application of a microbial culture for the biocatalysis of such hydroxyphosphinate compounds has recently been reported. [13][14][15] The first, but limited, application of biocatalysis in the deracemization of ethyl hydroxy(phenyl)methane(P-phenyl)phosphinate has also been reported. 15 Microbes preferentially hydrolyzed compound with an (S)-configuration at the a-carbon, whereas a lack of stereoselectivity was observed toward the phosphorus atom.…”

Biotransformations of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid and the determination of the absolute configuration of all isomers

“…Obtaining isomers with an absolute configuration of products of biotransformation dependent on the phosphorus atom is an unexpected result, because such compounds with two stereogenic centers have previously been obtained by biotransformation of the same or similar microorganisms, resulting in a high enantiomeric excess of isomers of (S) configuration on the a-carbon atom [16,17].…”

“…Cell cultures before biotransformations were grown in a medium tested previously for stimulating vigorous growth and lipolytic activity [16].…”