Synthesis and applications of diphosphine ligands derived from the lignan hydroxymatairesinol

• 4 Chiral diphosphines were prepared from the natural lignan hydroxymatairesinol.
• The phosphines were utilized in rhodium catalyzed hydrogenation of alkenes.
• High catalytic activity was observed with low catalyst loading.
• Hydrogenation of 1-acetamidostyrene gave up to 84% ee of the S-enantiomer.

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.

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