Pseudo enantiomeric mixed S/P ligands derived from carbohydrates for the 1,4-addition of phenyl boronic acid to cyclohexenone†
Abstract
The application of phosphinite–thioglycosides and phosphine–thioglycosides ligands in Rh(I)-catalyzed 1,4-addition of phenylboronic acid to cyclohexenone is reported. Among the ligands tested, phosphinite–thioglycoside 3 and phosphine–thioglycoside 10, bearing a 1,2-cis arrangement of the two heteroatoms, have exhibited the best results in terms of reactivity and enantioselectivity. Interestingly, ligands 3 and 10, both derived from a D-sugar are able to generate the addition product of the phenylboronic acid to the cyclohexenone with opposite configurations, behaving thus as enantiomers.
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