title: Catalytic, enantioselective synthesis of 1,2-anti-diols by asymmetric ring-opening/cross-metathesis.
abstract: 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.
authors.affiliation: Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA).
authors.forename: John
authors.initials: J
authors.lastname: Hartung
authors.forename: Robert H
authors.initials: RH
authors.lastname: Grubbs
mesh_terms: D000438:Alcohols; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D012428:Ruthenium
keywords: alcohols; asymmetric catalysis; metathesis; pheromones; ruthenium