Abstract
The 1,3-dipolar cycloadditions of the cyclic nitrones 1 and 2 to several γ-oxo α,β-unsaturated esters, 5-10, are reported. A strong predominance of the regioisomers with the oxygen atom of the dipole attached to the β-ester position is observed. This high regioselectivity is attributed to steric factors. The reduction of the carbonyl group of some of the major cycloadducts is a good yielding procedure for the preparation of some hydroxylic derivatives that are not formed or obtained only as minor stereoisomers in the cycloadditions of the same nitrones to the corresponding γ-hydroxy α,β-unsaturated esters.
| Original language | English |
|---|---|
| Pages (from-to) | 10857-10878 |
| Journal | Tetrahedron |
| Volume | 54 |
| Issue number | 36 |
| DOIs | |
| Publication status | Published - 3 Sep 1998 |
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Alibés, R., Busqué, F., De March, P., Figueredo, M., Font, J., & Parella, T. (1998). On the regioselectivity in nitrone cycloadditions to γ-oxo α,β- unsaturated esters. Tetrahedron, 54(36), 10857-10878. https://doi.org/10.1016/S0040-4020(98)00628-0