System. -A new route towards 1,4:2,5-dianhydroalditols by Pd 2+ -catalyzed bicyclization of sugar-derived alkenitols is developed. The reaction requires an all-syn configuration of the vinylic stereotriad. -(BABJAK, M.; REMEN, L.; SZOLCSANYI, P.; ZALUPSKY, P.; MIKLOS, D.; GRACZA*, T.; J. Organomet. Chem. 691 (2006) 5, 928-940; Dep. Org. Chem., Slovak Univ. Technol., SK-812 37 Bratislava, Slovakia; Eng.) -Nuesgen 25-163
Diastereoselective synthesis of trisubstituted tetrahydrofuran (D-lyxo-4) from the equimolar diastereomeric mixture of Derythro-/D-threo-1-pentenitols (1) is described. The synthesis exploits a sequence of two novel reactions: diastereospecific palladium(II)-catalyzed bicyclization of pentenitols 1 with degeneration of the allylic stereogenic center and subsequent regioselective ringopening of bicyclic skeleton 2.
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