Anionic species formed by treatment of vinyl sulfones with hydridoaluminates were trapped intramolecularly by esters to provide six- and seven-membered cyclic ketosulfones, e.g. I (R = Me, H, Ar = p-tolyl) and II, exemplified by the stereoselective construction of trans-hydrindanes and of perhydroazulenes. This led to formal syntheses of confertin (III) and damsinic acid.
- vinyl sulfones
Jones, D. N., Maybury, M. W. J., Swallow, S., & Tomkinson, N. C. O. (1993). Novel cyclizations involving vinyl sulfones: stereoselective construction of perhydroazulenes and trans-hydrindanes. Tetrahedron Letters, 34(52), 8553-8556. https://doi.org/10.1016/S0040-4039(00)61383-7