Titanium Tetrachloride Mediated Addition of 1,8-Bis(trimethylsilyl)-2,6-octadiene to Aldehydes. A One-Step Control of Four Stereogenic Carbon Centers

Article abstract of DOI:10.1021/jo00086a019

The addition reaction of 1,8-bis(trimethylsilyl)-2,6-octadiene with aliphatic aldehydes in the presence of titanium tetrachloride affords 2,5-divinylhexane-1,6-diols with very high diastereoselectivity (up to 90percent) and good yields (ca. 70-75percent).In the case of benzaldehyde, the structure of the adduct was established as the meso isomer (1S*,2R*,5S*,6R*)-1,6-diphenyl-2,5-divinyl-1,6-hexanediol by single-crystal X-ray analysis.