title: Chiral phosphoric acid directed regioselective acetalization of carbohydrate-derived 1,2-diols.
abstract: In control: A chiral phosphoric acid catalyst significantly enhances or completely overrides the inherent regioselective acetalization profiles exhibited by monosaccharide-derived 1,2-diol substrates. This study represents the first example of chiral-catalyst-directed regio- and enantioselective intermolecular acetalizations, which are complementary to existing methods for substrate-controlled functionalization of polyols.
authors.affiliation: Department of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA).
authors.forename: Enoch
authors.initials: E
authors.lastname: Mensah
authors.forename: Nicole
authors.initials: N
authors.lastname: Camasso
authors.forename: Will
authors.initials: W
authors.lastname: Kaplan
authors.forename: Pavel
authors.initials: P
authors.lastname: Nagorny
mesh_terms: D000085:Acetates / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D010756:Phosphoric Acids / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D002241:Carbohydrates; D010756:Phosphoric Acids; D011714:Pyrans; C030242:phosphoric acid
keywords: carbohydrates; organocatalysis; protecting groups; regioselectivity; synthetic methods