title: The oxide anion accelerated retro-diels-alder reaction.
abstract: 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.
authors.affiliation: Department of Chemistry and The Skaggs Institute of Chemical Biology The Scripps Research Institute 10550 North Torrey Pines Road, La Jolla, California 92037 (USA) and Department of Chemistry and Biochemistry University of California, San Diego 9500 Gilman Drive, La Jolla, California 92093 (USA) Fax: Int. code +(619) 784-2469.
authors.forename: M E
authors.initials: ME
authors.lastname: Bunnage
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
keywords: Diels-Alder reactions; oxide anion; pericyclic reactions; retro reactions; synthetic methods