A DFT study of 1,3-dipolar cycloaddition of cyclic nitrones to unsaturated lactones. Part II

Sebastian Stecko (1) , Konrad Pasniczek (1) , Carine Michel (2) , Anne Milet (2) , Serge Perez (3) , Marek Chmielewski (1)

1 IOC - Institute of Organic Chemistry
2 DCM - Département de Chimie Moléculaire
3 CERMAV - Centre de Recherches sur les Macromolécules Végétales

The 1,3-dipolar cycloadditions of cyclic nitrones to five-membered unsaturated lactones are studied. Special attention was focused on a single and double asymmetric induction when one or both components were chiral. The energies of the cycloaddition reactions are investigated through application of molecular orbital calculations at the B3LYP/6-31+G(d) theory level. A study of the different reactants’ approaches and their conformational aspects revealed the stereochemical preferences of these reactions. The results of these calculations correspond well with the previously reported experimental data.

Domaines: Chimie

Sebastian Stecko, Konrad Pasniczek, Carine Michel, Anne Milet, Serge Perez, et al.. A DFT study of 1,3-dipolar cycloaddition of cyclic nitrones to unsaturated lactones. Part II. Tetrahedron: Asymmetry, 2008, 19 (18), pp.2140-2148. ⟨10.1016/j.tetasy.2008.09.003⟩. ⟨hal-00352480⟩