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 |
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Pages (from-to) | 10857-10878 |
Journal | Tetrahedron |
Volume | 54 |
Issue number | 36 |
DOIs | |
Publication status | Published - 3 Sep 1998 |