575450-58-7Relevant academic research and scientific papers
1,3-Dipolar cycloadditions of D-erythrose- and D-threose-derived alkenes with nitrones
Blanarikova-Hlobilova, Iva,Fisera, Lubor,Pronayova, Nad'A,Koman, Marian
, p. 951 - 964 (2003)
The new chiral terminal alkenes derived from cyclic acetals of D-erythrose 1-3 and D-threose 5, 6 were prepared. The alkenes 1, 2 and 5 react with chiral nitrones to afford the corresponding diastereomeric isoxazolidines 19-21. The stereoselectivity was dependent on the steric hindrance of the nitrone. In all cases the cycloadditions are endo-selective. The major products were found to have the C-3/C-4 erythro- and C-3/C-3a cis-configuration. Its formation can be rationalized by a less hindered endo-attack of the (Z)-nitrone in an antiperiplanar manner with respect to the largest group of the cyclic acetal.
