Divergent enantioselective synthesis of (P)- and (M)-dihydro5helicenequinones from a common tetrahydroaromatic precursor

The domino asymmetric Diels–Alder reaction/spontaneous sulfoxide elimination process between a vinyl dihydrophenanthrene as diene and enantiopure (SS)-2-(p-tolylsulfinyl)-1,4-benzoquinone gave access to a tetrahydroaromatic pentacyclic derivative possessing central chirality which led, in a divergent way, to helically chiral (P) or (M) enantiomers of dihydro5helicenequinones in good to excellent chemical and optical yields simply by selecting the appropriate oxidant reagent which makes the final aromatization.