The preparation and subsequent Diels–Alder addition reactions of chiral 9-functionalised anthracene derivatives have been investigated. 9-(1-Methoxyethyl) anthracene undergoes highly diastereoselective (> 95∶ 5) thermal and photoinduced Diels–Alder additions with maleic anhydride and N-methylmaleimide. The corresponding reactions of 1-anthracen-9- ylethanol occur with the reverse sense of selectivity for additions with maleic anhydride ...
