REDUCTIVE COUPLING OF α,β-ENONES I : REDUCTION OF METHYL-VINYL KETONE AND MESITYL OXIDE.

Article abstract of DOI:10.1016/S0040-4039(01)82039-6

Reductive coupling of methyl-vinyl ketone with TiCl4-Mg gives pinacol 1 (25percent).According to the reducing agents, mesityl oxide yields 2,4,5,7-tetramethyl-octa-2,4,6-triene 3 (with 4TiCl3-LiAlH4), triene 3 or 2,4,5,7-tetramethyl-octa-2,6-dien-4,5-diol 5 (with TiCl4-Mg), pinacol 5 (with VCl3-Mg), and 2-acetyl-1,3,3,4,4-pentamethyl-cyclopentene 7 (with CrCl3-Mg or FeCl3-Mg or ZrCl4-Mg) as major products.