title: Design of a binaphthyl-based axially chiral amino acid as an organocatalyst for direct asymmetric aldol reactions.
abstract: A novel and robust binaphthyl-based amino acid was designed and successfully applied to the direct asymmetric aldol reaction. In some cases, this catalyst leads to higher yields and selectivities than the well-known proline catalyst. For instance, the direct asymmetric aldol reaction of acetone with 4-nitrobenzaldehyde in the presence of the binaphthyl-based amino acid catalyst proceeded smoothly to give the aldol adduct in 82% yield with 95% ee. This catalyst was also found to catalyze effectively the reactions of cyclic or unsymmetrical ketones to give the corresponding aldol adducts with excellent diastereo- and enantioselectivities.
authors: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
authors: Taichi
authors: T
authors: Kano
authors: Osamu
authors: O
authors: Tokuda
authors: Jun
authors: J
authors: Takai
authors: Keiji
authors: K
authors: Maruoka
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D009281:Naphthalenes