posted on 2021-07-20, 18:07authored byKevin
A. Scott, Jeffrey R. Groch, Isaac Chogii, Michael D. Delost, Pradipta Das, Jon T. Njardarson
The efficient assembly of complex
aromatic structures from simple
acyclic building blocks is reported. An anion-cascade union of an
enoate and a conjugated imine affords cyclohexenone products, which
are readily aromatized to phenols. By engaging the intermediate cyclohexenones
with Grignard reagents, a facile addition/elimination proceeds yielding
chiral cyclohexadienes, which are then aromatized. In a complementary
approach, the cyclohexenone products are converted into enol triflates,
which provides a gateway to diverse aromatic architectures following
cross-couplings and aromatization steps.