Heiner, Thomas; Kozhushkov, Sergei I.; Noltemeyer, Mathias; Haumann, Thomas; Boese, Roland; de Meijere, Armin:

Intramolecular Diels-Alder reactions of furans with a merely strain-activated tetrasubstituted alkene: bicyclopropylidene.

In: Tetrahedron (Tetrahedron), Jg. 52 (1996) ; Nr. 37, S. 12185-12196
ISSN: 0040-4020
Zeitschriftenaufsatz / Fach: Chemie
Bicyclopropylidene derivs., e.g., I (R = H, OMe), with furan moieties attached on tethers of various length and nature all undergo clean intramol. Diels-Alder reactions with complete endo-diastereoselectivities when heated to 70 - 130 DegC, under 10 kbar pressure. The reaction rates are at least as high or higher than those of analogously tethered methylenecyclopropane-furan derivs., e.g., II, in spite of the fact that the reactive double bond in bicyclopropylidene is tetrasubstituted and not activated by any electron withdrawing group.