The Application of 2‑Benzyl-1,4-naphthoquinones as Pronucleophiles in Aminocatalytic Synthesis of Tricyclic Derivatives

This
study demonstrates an unprecedented reactivity of 2-substituted-1,4-naphthoquinones.
By applying the principle of vinylogy, they have been employed as
vinylogous pronucleophiles in the organocatalytic cascade reaction
for the first time. This novel catalytic activation of 1,4-naphthoquinones
enables access to carboannulated naphthalen-1­(4H)-one
derivatives of biological importance. The site-selectivity and stereoselectivity
of a process proved possible to control by the proper choice of reaction
conditions.