부산대학교 도서관

Here we present a transition metal-free synthesis of a rigid, orthogonally functionalized bicyclic sulfone, starting from readily available reagents. The transformation proceeds via a tandem vinylogous 1,2-addition/anionic oxy-Cope sequence, followed by a second vinylogous ketone addi- tion. Stereochemical assignments suggest that the anionic oxy-Cope reaction proceeds exclusively through a boat- shaped transition state. The product of the two-step sequence can be further functionalized through subsequent chemo- and diastereoselective transformations, suggesting possible applications in medicinal chemistry or materials chemistry. [ABSTRACT FROM AUTHOR]