Publication details
Stereoselectivity of 1,3-dipolar cycloadditions of D-erythrose and D-threose derived nitrones with methyl acrylate
| Authors | |
|---|---|
| Year of publication | 2001 |
| Type | Article in Periodical |
| Magazine / Source | Synlett |
| MU Faculty or unit | |
| Citation | |
| Keywords | cycloadditions; nitrones; isoxazolidines; stereoselectivity; heterocycles |
| Description | 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. |