Enzymatic resolution of α-hydroxyphosphinates with two stereogenic centres and determination of absolute configuration of stereoisomers obtained

Research paper Microbial biotransformation of two phosphonoacetic acid derivatives bearing two stereomeric centres

“…3). However, previous experiments on structurally similar compounds with the use of analogical method Majewska et al, 2009) and deductive analysis of the obtained data allowed us to cautiously assign NMR signals to eantiomers and diastereomers. The starting substrate is a mixture of four stereoisomers --two enantiomeric mixtures of diastereomers (denoted as A and B).…”

“…Our earlier studies, aimed at obtaining pure enantiomers of organophosphonic compounds, demonstrated that some hydroxyphosphonates might be delivered with good or excellent enantioselectivity by means of biotransformations (Skwarczyński et al, 1999;Malinowska et al, 2011). It was also found that analogous compounds like hydroxyphosphinates, may be produced in a similar way Majewska et al, 2009).…”

Computer-Aided Optimization of Phosphinic Inhibitors of Bacterial Ureases

“…Because the formation of phosphorus−carbon bonds via addition of phosphinic acid derivatives to aldehydes is well acknowledged, − this strategy was applied for the synthesis of the central building block 9 which contains a hydroxymethyl group. Indeed, by condensation of the Cbz-protected methyl phosphinate analogue of glycine 8 with paraformaldehyde in the presence of triethylamine, the hydroxymethylphosphinate 9 was obtained in moderate yield (Scheme ).…”

Quinine as a highly responsive chiral sensor for the 1H and 19F NMR enantiodiscrimination of N-trifluoroacetyl amino acids with free carboxyl functions

“…1) has been recognized for a long time. [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] Alkaloid Qui represents a multireceptor chiral auxiliary endowed with two rigid moieties, i.e. the aromatic quinoline ring and the quinuclidine bicycle, which are connected by potentially freely rotating bonds and, hence, are able to shape Qui conformation on the basis of the stereoelectronic requirements of interacting enantiomeric substrates.…”