The oxide anion accelerated retro-Diels-Alder reaction

The widespread application of the retro-Diels-Alder reaction in synthesis has been hampered by the high temperatures usually required to effect cycloreversion. The discovery of the anionic oxy-Cope reaction was followed by predictions that the accelerating effect of the oxide anion should also be observed with other pericyclic reactions. Recently, such predictions have been confirmed for the retro-Diels-Alder reaction, which often proceeds rapidly at room temperature by oxide anion rate acceleration. Such mild retro-Diels-Alder reactions have now been employed in the synthesis of a range of molecular targets, including temperature-sensitive enediynes.