Diastereoselective intermolecular addition of the 1,3-dioxolanyl radical to N-acyl aldohydrazones. Asymmetric synthesis of alpha-amino acid derivatives.
[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.
Fernández
Marta
M
Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
Alonso
Ricardo
R
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D006835:Hydrazones