title: One-Pot Domino Aldol Reaction of Indium Enolates Affording 6-Deoxy-α-D,L-altropyranose Derivatives: Synthesis, Mechanism, and Computational Results.
abstract: The domino-aldol-aldol-hemiacetal-reaction cascade of indium and other group 13 metal enolates furnished 6-deoxy-α-D,L-altropyranose derivatives in up to 99% yield under thermodynamic control. At lower temperature and thus under kinetic control, the reaction proceeded in a much less diastereoselective manner. The changeover from kinetic to thermodynamic control operating in this multistep domino-aldol-aldol-hemiacetal protocol was used for probing the efficiency of DFT computations. Calculations at the B3LYP/6-31G(d)/LANL2DZ level provided a mechanistic picture in full agreement with the experimental outcome.
authors.affiliation: Department Chemie-Biologie, Universität Siegen, Adolf-Reichwein-Strasse 2, D-57068 Siegen, Germany.
authors.forename: M Emin
authors.initials: ME
authors.lastname: Cinar
authors.affiliation: Department Chemie-Biologie, Universität Siegen, Adolf-Reichwein-Strasse 2, D-57068 Siegen, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Schmittel
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry; D007204:Indium / Q000737:chemistry*; D007700:Kinetics; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D002264:Carboxylic Acids; D009005:Monosaccharides; D007204:Indium