Problems and exercisesAsymmetric metal catalysis: Sharpless and Noyori
Exercise 1
What product is obtained in the Sharpless epoxidation of (E)-hex-2-en-1-ol with D-(−)-diethyl tartrate? Why is the C2=C3 double bond of geraniol epoxidized and not the more electron-rich C6=C7? Would geranyl methyl ether react?
Exercise 2
Which reagent would you use to obtain (S,S)-1,2-diphenylethane-1,2-diol from trans-stilbene? What roles do the potassium osmate, the ligand and the potassium ferricyanide of AD-mix play? What would be obtained from cis-stilbene with OsO4 and NMO, without a ligand?