REDUCTIVE COUPLING OF (R)-(+)-CARVONE AND (+)-CAMPHOR BY THE TiCl4-Mg REAGENT. X-RAY CRYSTAL STRUCTURE OF (+)-(1S, 5R, 1'S, 5'R)-CARVONE PINACOL

Article abstract of DOI:10.1016/S0040-4039(00)82228-5

The reductive coupling of (R)-(+)-carvone by TiCl4-Mg-tBuOH leads to (+)-(1S, 5R, 1'S, 5'R)-carvone pinacol 3 (70 percent).In presence of pentane, (-)-(1R, 5R, 1'R, 5'R)-carvone pinacol 4 (50 percent) and ketol 5 (15 percent) are isolated.Isoborneol (58 percent) and borneol (32 percent) result of the reduction of (+)-camphor with the same reagent.