A convenient route from simple sugars to new chiral bis(phosphinoesters) for asymmetric catalysis

Readily available chiral bis(phosphinoesters) based on d-glucose, d-mannose and d-galactose have been prepared in only two steps and in large scale starting from inexpensive commercial precursors. Their Pd complexes catalyze the asymmetric desymmetrization of meso-cyclopent-4-ene-1,3-diol biscarbamate in ee’s up to 82%.

Graphical abstractReadily available chiral bis(phosphinoesters) based on d-glucose (2G), d-mannose (2M) and d-galactose (2Gt) have been prepared starting from inexpensive commercial precursors. Their Pd complexes catalyze the asymmetric desymmetrization of meso-cyclopent-4-ene-1, 3-diol biscarbamate (4) affording 5 in ee’s up to 82%.Figure optionsDownload full-size imageDownload as PowerPoint slide