Recent advances in isolation of the lignan hydroxymataresinol (HMR) from Norway Spruce (Picea abies) promped us to use it (HMR) as a novel chiral starting material for syntheses of chiral phosphine DIOP-type ligands. Highly efficient routes for syntheses of various phosphines were developed. The routes include different modifications of the lignan skeleton followed by the reduction of the lactone ring, preparation of the dimesylate derivative and substitution of the mesylates with the phosphide anion (Fig. 1 and 2). Several rhodium(I) complexes were prepared (Figure 2). There use as asymmetric transition metal catalysts is under development in our laboratory.

Syntheses and applications of chirally pure phosphine ligands from the natural lignan hydroxymataresinol

243rd National Meeting (2012)

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