Asymmetric Dihydroxylation Enables Rapid Construction of Chiral Dendrimers Based on 1,2‐Diols

Ninety chiral centers and a molecular mass of 11354 Da are the outstanding features of the largest C3‐symmetric, chiral dendrimer to date. As general approach to these chiral polyether compounds (1) styrenes or stilbenes are converted into 1,2‐diols by asymmetric dihydroxylation; (2) the resulting building blocks are then linked together to form dendrons by a uniquely effective ether‐forming reaction, in which the vincinal hydroxyls are alkylated with benzylic bromides by using KOH pellets in refluxing toluene; (3) the dendrons are coupled to a core unit such as 1,3,5‐benzene‐tricarbonyl trichloride.