title: Site-selective catalysis: toward a regiodivergent resolution of 1,2-diols.
abstract: This paper demonstrates that the secondary hydroxyl can be functionalized in preference to the primary hydroxyl of a 1,2-diol. The site selectivity is achieved by using an enantioselective organic catalyst that is able to bond to the diol reversibly and covalently. The reaction has been parlayed into a divergent kinetic resolution on a racemic mixture, providing access to highly enantioenriched secondary-protected 1,2-diols in a single synthetic step.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
authors.forename: Amanda D
authors.initials: AD
authors.lastname: Worthy
authors.forename: Xixi
authors.initials: X
authors.lastname: Sun
authors.forename: Kian L
authors.initials: KL
authors.lastname: Tan
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D007700:Kinetics; D013237:Stereoisomerism
chemical_list: D000438:Alcohols