Synthesis of 6-Substituted Piperidin-3-ones via Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles with Electron-Rich Aromatic Nucleophiles.

A highly diastereoselective rhodium(II)-catalyzed transannulation of aldehyde-tethered N-sulfonyl triazoles with electron-rich aromatic nucleophiles is reported for the first time to afford functionalized 6-substituted piperidin-3-ones. The reaction has a broad substrate scope including both aliphatic and aromatic N-sulfonyl-1,2,3-triazoles together with various aromatic nucleophiles. The addition of a catalytic amount of Lewis acid has proven to be crucial for the yield improvement. By employing this methodology, hardly accessible piperidin-3-ones bearing quaternary carbons could be obtained.