Tetrahedron

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

T Heiner, SI Kozhushkov, M Noltemeyer, T Haumann…

Index: Heiner, Thomas; Kozhushkov, Sergei I.; Noltemeyer, Mathias; Haumann, Thomas; Boese, Roland; De Meijere, Armin Tetrahedron, 1996 , vol. 52, # 37 p. 12185 - 12196

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Citation Number: 42

Abstract

Bicyclopropylidene derivatives 1, 6, 8 with furan moieties attached on tethers of various length and nature all undergo clean intramolecular Diels-Alder reactions with complete endo-diastereoselectivities when heated to 70–130° C, under 10 kbar pressure. The reaction rates are at least as high or higher than those of analogously tethered methylenecyclopropane-furan derivatives 15, 17, 20, in spite of the fact that the reactive ...

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