The Diels-Alder Chemoselectivity of 3,4,6,7-Tetramethylidenebicyclooctane-2-exo,8-syn-diyl Derivatives

Article abstract of DOI:10.1002/hlca.19920750412

Strong dienophiles prefer to add onto the diene moiety attached at C(2), C(3) of 2,3,6,7-tetramethylidenebicyclo<3.2.1>octane ((+/-)-1; see Scheme I), whereas in the case of 3,4,6,7-tetramethylidenebicyclo<3.2.1>octane-2-exo,8-syn-diyl derivatives, the diene moiety at C(6), C(7) reacts faster than at C(3), C(4), as long the bulk of the 8-syn-substituent is large enough (see Schemes 2 and 3).