J.-L. Metral, J. Lauterwein, P. Vogel
Sep 10, 1986
Citations
0
Influential Citations
20
Citations
Journal
Helvetica Chimica Acta
Abstract
The syntheses of 2,3-dimethylidene- and 2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptanes substituted in position C(1) are reported. The 1-dimethoxymethyl group in derivatives 2 and 6 controls the regioselectivity of the Lewis-acid-catalyzed Diels-Alder additions with methyl vinyl ketone and butynone. For the EtAlCl2-catalyzed addition of methyl vinyl ketone to 6, the regioselectivity can be reversed by a small solvent modification. The tetraene 2 is a versatile reagent for regioselective ‘tandem’ cycloadditions.