TITANIUM TETRACHLORIDE MEDIATED ADDITION OF 1,8-BIS(TRIMETHYLSILYL)-2,6-OCTADIENE TO ALDEHYDES - A ONE-STEP CONTROL OF 4 STEREOGENIC CARBONCENTERS

Authors
PELLISSIER H TOUPET L SANTELLI M
Citation
H. Pellissier et al., TITANIUM TETRACHLORIDE MEDIATED ADDITION OF 1,8-BIS(TRIMETHYLSILYL)-2,6-OCTADIENE TO ALDEHYDES - A ONE-STEP CONTROL OF 4 STEREOGENIC CARBONCENTERS, Journal of organic chemistry, 59(7), 1994, pp. 1709-1713
Citations number
68
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
7
Year of publication
1994
Pages
1709 - 1713
Database
ISI
SICI code
0022-3263(1994)59:7<1709:TTMAO1>2.0.ZU;2-H
Abstract
The addition reaction of 1,8-bis(trimethylsilyl)-2,6-octadiene with al iphatic aldehydes in the presence of titanium tetrachloride affords 2, 5-divinylhexane-1,6-diols with very high diastereoselectivity (up to 9 0%) and good yields (ca. 70-75%). In the case of benzaldehyde, the str ucture of the adduct was established as the meso isomer ,5S*,6R*)-1,6 -diphenyl-2,5-divinyl-1,6-hexanediol by single-crystal X-ray analysis.