Titanium-mediated and neighboring-group-assisted d-methylation of homoallyl alcohols: a new regio- and stereoselective carbon-carbon linking reaction

Upon treatment with Me2TiCl2 or Me3Al in the presence of TiCl4, an H atom at the olefinic 4-position is replaced by a Me group. Terminal homoallyl alcs. afford E isomers. If the double bond is internal, the C chain (at the other side of the OH group) gives up its original position to the entering Me group and switches to the other one at the same C atom. [on SciFinder (R)]


Published in:
Chemistry Letters, 11, 1819-22
Year:
1982
Keywords:
Note:
CAN 98:71442
23-7
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0366-7022
written in English.
75-24-1 Role: RCT (Reactant), RACT (Reactant or reagent) (catalysts contg. titanium tetrachloride and, for d-methylation of homoallyl alc.); 7550-45-0 Role: USES (Uses) (catalysts contg. trimethylaluminum and, for d-methylation of homoallyl alc.); 763-89-3P; 764-37-4P; 1594-24-7P; 2004-67-3P; 19639-97-5P; 21019-60-3P; 54560-70-2P; 58927-81-4P; 63714-11-4P; 84376-40-9P; 84415-81-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 624-97-5; 627-27-0; 763-32-6; 764-37-4; 928-96-1; 928-97-2; 1838-77-3; 4516-90-9 Role: RCT (Reactant), RACT (Reactant or reagent) (d-methylation of)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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