Maleic anhydride and cyclopentadiene undergo this reaction very quickly since the former has electron-withdrawing groups and the latter is locked in the s-cis confirmation.
EJ Corey's total synthesis of Tamiflu begins with one of these reactions, and most norbornene derivatives are synthesized using this reaction. Niobium-5-Chloride is used to activate molecules for this reaction, and dendralene has the ability to undergo this reaction several times in tandem. Maleic anhydride and cyclopentadiene undergo this reaction very quickly since the former has electron-withdrawing groups and the latter is locked in the s-cis confirmation. The LUMO of one reactant and the HOMO of the other has to overlap correctly in this reaction, which occurs preferentially in the endo confirmation. It is a 4+2 cycloaddition that occurs in a single, concerted step, and creates a cyclohexene derivative. For 10 points, name this organic reaction in which a diene reacts with a dienophile.
EJ Corey's total synthesis of Tamiflu begins with one of these reactions, and most norbornene derivatives are synthesized using this reaction.
{Diels}-{Alder} Reaction