A Unique Skeletal Rearrangement of a Bicyclo[3.3.1]nonanetrione to a Tetrahydroquinolin-2(1H)-one System.

The unexpected formation of a 4-hydroxytetrahydroquinolin-2(1H)-one from a bicyclo[3.3.1]nonanetrione system and an amino alcohol in the presence of TsOH is reported. The mechanism of this transformation was studied by DFT calculations. The reaction provides an entry to the synthesis of highly functionalized 4-hydroxytetrahydroquinolin-2(1H)-ones. [ABSTRACT FROM AUTHOR]