Asymmetric dihydroxylation of aryl allyl ethers

Article abstract of DOI:10.1016/S0040-4039(00)77590-3

Asymmetric dihydroxylation of substituted aryl allyl ethers is described. Para-substituents are shown to favor high enantioselectivity (89-95%ee), while ortho-groups have a deleterious effect (28-63%ee). Four medicinal agents were prepared: guaifenesin (expectorant), mephenesin (muscle relaxant), chlorphenesin (antifungal) and propanolol (β-blocker).