First example of an atropselective dehydro-Diels–Alder (ADDA) reaction

A new concept of a stereoselective synthesis of axially chiral biaryls, formed in the course of the dehydro-Diels–Alder (DDA) reaction, has been disclosed. It is based on asymmetric induction of the newly formed chirality axis by a chirality center, which is present in the two synthesized DDA reactants. Depending on the different length of the linkers joining the alkyne moieties the DDA reaction may be triggered photochemically or thermally, where only the thermal variant was stereoselective.