Theoretical and experimental determination of the effects governing the transannular Diels-Alder reaction of trans-trans-cis systems with or without activation of the dienophile
S. Fortin et al., Theoretical and experimental determination of the effects governing the transannular Diels-Alder reaction of trans-trans-cis systems with or without activation of the dienophile, J AM CHEM S, 123(34), 2001, pp. 8210-8216
A thorough study of the transannular Diels-Alder (TADA) reaction of trans-t
rans-cis macrocyclic trienes was carried out. It led to a better understand
ing of various parameters that govern the TADA reaction in particular and t
he Diels-Alder reaction in general. Thus, carbonyl activation of the dienop
hile and substitution of the diene are discussed, as well as the presence o
f substituents on the macrocycle and their respective effects at the transi
tion-state level.