Synthesis of recyclable fluorous chiral ligands and evaluation of their catalytic activity toward asymmetric addition of dimethylzinc to aldehydes

Chemistry, an Asian Journal
Yasser S SokeirikAkira Ando

Abstract

The asymmetric addition of Me(2)Zn to aldehydes is very slow and mostly gives low ee values. Previously, we reported the synthesis of a fluorous chiral ligand, (4R,5S,alpha'R)-2,2-dimethyl-alpha,alpha,alpha'-tris(perfluorooctyl)-2,3-dioxolane-4,5-dimethanol (1 a), derived from tartarate as a chiral pool. Ligand 1 a showed high activity toward the addition of Me(2)Zn to aldehydes with high enantiomeric excess. However, the very high content of fluorine makes 1 a difficult to dissolve in common solvents; hence, much solvent is required, which limits its use. This report describes the modification of 1 a by replacing either the perfluorooctyl groups with shorter perfluoroalkyl ones or the acetone ketal part with cyclohexanone ketal. The perfluorobutyl analogue 1 c is much more soluble than 1 a and shows comparable asymmetric induction toward the addition of Me(2)Zn to aldehydes. Furthermore, 1 c has a much lower molecular weight than 1 a. This means that 1 c is used in smaller amounts (weight) than 1 a. The cyclohexanone ketal analogue 1 d is more soluble than 1 a and more easily synthesized owing to its high solubility and ease of crystallization. Ligand 1 d showed much higher asymmetric induction toward cyclohexanecarbaldehyde, ...Continue Reading

References

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