First example of an antibody-catalyzed aza Diels-Alder reaction.

Described herein is the synthesis of a hapten of biocyclo[2,2,2]octene 5 designed to mimic the exo transition-state of an aza Diels-Alder reaction. Immunization of rabbits with this hapten provided polyclonal antibodies, Aza-BSA-3, which were used to synthesize adduct 4b in the first reported antibody-catalyzed exo Diels-Alder reaction.