Ferrocenyl chalcones

Wu X, Tiekink ERT, Kostetski I, Kocherginsky N, Tan ALC, Khoo SB, Wilairat P, Go M-L (2006) Antiplasmodial activity of ferrocenyl chalcones investigations into the role of ferrocene. Eur J Pharm Sci 27 175-187... 

A series of ferrocenyl chalcones as exemplified by the two compounds in Fig. 12 were evaluated for in vitro antimalarial activity against the K1 CQ-resistant strain. Disappointing low activities in the micromolar range were reported [100]. 

The copper-catalysed enantioselective 1,4-conjugate addition of Et2Zn to chalcones was investigated in the presence of a catalytic amount of Af,P-ferrocenyl ligand (179) with central and planar chirality under mild conditions (0 °C to room temper- ature). Chalcones with ortho-substituents (from ortho-substituted benzaldehydes and acetophenones) exhibited a dramatic improvement in the enantioselectivities (<92% ee).229... 

Chiral Catalysts Containing Group 10 Metals (Ni, Pd, and Pt). The catalyst formed in situ from Ni(acac)2 and bomane aminoalcohols (DAB or DAIB) catalyze the enantioselective addition of diethylzinc to chalcones (254) (Fig. 21). Nickel(II)-chiral Schiff-base (the ligand derived from 1,2-diaminocyclohexane or 1,2-diaminopropane with pyrone derivative) complexes were efficient in epoxida-tion of nonfunctionalized olefins (255). Bis-ferrocenyl-triphosphane (PIGIPHOS) formed catalytically active complex with Ni(II) (256). Nickel-catalyzed asymmetric hydrocyanation of vinylarenes using glucose-derived phosphinite ligands was observed (257). 

The cyanomethyl anion dimerizes first before adding to ferrocenyl-substituted chalcones. Cyanopyridines are formed in high yields. ... 

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