Catalytic, enantioselective synthesis of 1,2-anti-diols by asymmetric ring-opening/cross-metathesis

Article abstract of DOI:10.1002/anie.201310767

An enantioselective method for the synthesis of 1,2-anti-diols has been developed. A cyclometalated chiral-at-ruthenium complex catalyzes the asymmetric ring-opening/cross-metathesis of dioxygenated cyclobutenes, thus resulting in functionally rich synthetic building blocks. Syntheses of the insect pheromone (+)-endo-brevicomin and monosaccharide ribose demonstrate the synthetic utility of the 1,2-anti-diol fragments generated in the title reaction. Rather fetching: Chiral vicinal diols are found in natural products and ligands used for asymmetric catalysis. The enantioselective ring-opening/cross-metathesis of disubstituted cyclobutenes has been carried out with an enantiopure ruthenium metathesis catalyst to afford 1,2-anti-diols with high enantiopurity. The synthetic versatility of the products was demonstrated in the synthesis of insect pheromone (+)-endo-brevicomin and a monosaccharide ribose.