Informace o publikaci
Stereoselectivity of 1,3-dipolar cycloadditions of D-erythrose and D-threose derived nitrones with methyl acrylate
| Autoři | |
|---|---|
| Rok publikování | 2001 |
| Druh | Článek v odborném periodiku |
| Časopis / Zdroj | Synlett |
| Fakulta / Pracoviště MU | |
| Citace | |
| Klíčová slova | cycloadditions; nitrones; isoxazolidines; stereoselectivity; heterocycles |
| Popis | 1,3-Dipolar cycloadditions between the D-erythrose and D-threose derived nitrones and methyl acrylate proceed in a regiospecific manner to afford the corresponding 3,5-disubstituted diastereomeric isoxazolidines in good yields. The stereoselectivity was dependent on the steric hindrance of the nitrone. The major products were found to have the C-3/C-4' erythro and C-3/C-5 cis relative configuration. Its formation can be rationalized by less hindered endo attack of the Z-nitrone in an antiperiplanar manner with respect to the largest group of the cyclic acetal. |