Abstract
A rapid and facile method of accessing 4-phenyl-beta-keto-alpha-tetralones is reported. The key homo-Nazarov cyclization was achieved via treatment of the preceding phenylcyclopropane with TiCl4 at below ambient temperatures. In contrast to previous work, which was limited to electron-rich substrates, the present transformations proceeded without heating and were applicable to an electronically broad range of substrates. Furthermore, a mechanistically novel reaction afforded an unexpected gamma-diarylketone as well as a rearranged regioisomer of the expected alpha-tetralone.