Journal of Organic Chemistry p. 1709 - 1713 (1994)
Update date:2022-09-26
Topics:
Pellissier, Helene
Toupet, Loiec
Santelli, Maurice
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.
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