Synthesis of D-Erythrose and D-Threose Derived Nitrones and Cycloaddition to Styrene.
| Authors | |
|---|---|
| Year of publication | 1999 |
| Type | Article in Periodical |
| Magazine / Source | Tetrahedron |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Description | The new nitrones derived from cyclic acetals of D-erythrose (2a-c) and D-threose (8) react with styrene to afford the corresponding 3,5-disubstituted diastereomeric isoxazolidines 3-6 and 9-12. The stereoselectivity was dependent on the steric hindrance of the nitrone. The major products 3a-c (55-58 %) and 9 (73 %) were found to have the C-3/C-4' erythro and C-3/C-5 cis relative configuration by X-ray analysis. 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. (C) 1999 Elsevier Science Ltd. All rights reserved. |
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