Synlett · 1994 · 50 citations · 0 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryCross-coupling ReactionsHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsMacrocycle SynthesisOrganic Synthesis[4+2] CycloadditionAlkyne Cycloaddition ReactionsAsymmetric Heterocycle SynthesisCatalytic SelectivityHeck ReactionOne-pot DeprotectionRing-forming ReactionsTransition-metal-catalyzed Heterocycle Synthesis
Under catalytic conditions, (3.5 mol% Pd(OAc)2, 1.2 equiv. Ag2CO3 in acetonitrile) 2-bromo-1,6-diene 6 furnishes bis (exomethylene)cyclopentane 7. When generated in the presence of a dienophile, 7 immediately undergoes a Diels-Alder reaction; [4+2]-cycloadducts of 7 were thus prepared with a variety of dienophiles in a one-pot procedure in high yields.