Highly efficient methods for synthetic modifications of the natural lignan hydroxymatairesinol into chiral diphosphines similar to DIOP were developed. Catalytic activity and induction of enantioselectivity for the prepared phosphines were evaluated in rhodium catalyzed hydrogenations of different functionalized alkenes. High catalytic activities were observed with low catalyst loading at atmospheric pressure. The phosphines showed moderate to high enantioselectivity depending on the substrate used. Hydrogenation of 1-acetamidostyrene gave 84% ee of the S-enantiomer. (C) 2014 Elsevier B.V. All rights reserved.