Diastereomeric control of photoinduced Diels–Alder reactions of 1-anthracen-9-yl-ethanol by hydrogen-bonding effects

Photoinduced Diels–Alder reactions of 1-anthracen-9-yl-ethanol with maleic anhydride proceed with high diastereoselection but with complete reversal of the sense of selectivity compared to analogous O-methyl compound. Hydrogen-bonding effects have been established as the predominant factors in determining this selectivity.