SAKURAI REACTION ADDITION OF 1,8-BIS(TRIMETHYLSILYL)-2,6-OCTADIENE TOALPHA,BETA-ENONES - A ONE-STEP CONTROL OF 4 STEREOGENIC CARBON CENTERS

Authors
PELLISSIER H TOUPET L SANTELLI M
Citation
H. Pellissier et al., SAKURAI REACTION ADDITION OF 1,8-BIS(TRIMETHYLSILYL)-2,6-OCTADIENE TOALPHA,BETA-ENONES - A ONE-STEP CONTROL OF 4 STEREOGENIC CARBON CENTERS, Journal of organic chemistry, 63(7), 1998, pp. 2148-2153
Citations number
91
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
7
Year of publication
1998
Pages
2148 - 2153
Database
ISI
SICI code
0022-3263(1998)63:7<2148:SRAO1T>2.0.ZU;2-C
Abstract
The addition reaction of 1,8-bis(trimethylsilyl)-2,6-octadiene with op en-chain conjugated enones in the presence of titanium tetrachloride a ffords 4,7-divinyldecane-1,10-diones with very high diastereoselectivi ty. In the case of benzalacetone (trans-4-phenyl-3-buten-2-one), the s tructure of the adduct (74% yield) was established as the meso isomer ,9R*)-4,9-diphenyl-5,8-divinyldodecane-2,11-dione by a single-crystal X-ray analysis.