title: Diastereoselective intermolecular addition of the 1,3-dioxolanyl radical to N-acyl aldohydrazones. Asymmetric synthesis of alpha-amino acid derivatives.
abstract: [reaction: see text] N-Acyl aldohydrazones I (R = CO(2)Et, alkyl, aryl, and furyl) efficiently trap the 1,3-dioxolanyl radical intermolecularly without external activation at temperatures as low as -78 degrees C. For alkyl aldohydrazones, good diastereoselectivities are obtained in the presence of InCl(3) at low temperature. Elaboration of the adducts (II) allows for the asymmetric synthesis of alpha-amino acid derivatives.
authors.affiliation: Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
authors.forename: Marta
authors.initials: M
authors.lastname: Fernández
authors.forename: Ricardo
authors.initials: R
authors.lastname: Alonso
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D006835:Hydrazones