Phosphonoselenoic acid esters from the reaction between phosphoroselenoyl chlorides and Grignard reagents: synthetic and stereochemical aspects

Abstract

Substitution reactions between a phosphoroselenoyl chloride and Grignard reagents proceeded smoothly at the phosphorus atom to furnish phosphonoselenoic acid esters. The resulting mixture of diastereoisomers could be readily distinguished on the basis of ³¹P NMR, and separated by recrystallization or column chromatography to afford diastereoisomerically enriched products. For one of these diastereoisomers, the absolute configuration was determined by carrying out a single-crystal X-ray diffraction analysis.