New 5,5'-disubstituted BINAP derivatives : Syntheses and pressure and electronic effects in Rh asymmetric hydrogenation

Abstract A library of 5,5′-disubstituted BINAP derivatives were synthesized in good yield from optically pure BINAP and evaluated for the Rh-catalyzed homogeneous asymmetric hydrogenation of (α)-acylaminoacrylate ester, with ee of up to 77% being obtained with the phenyl derivative. The enantiomeric excess variation was followed according to the groups introduced in the 5,5′-position of BINAP and for a range of pressure from 5 to 30 bar.