Under carefully chosen working conditions (solvent, temp.), methyltitanium reagents smoothly convert homoallyl alcs. having a terminal double-bond into (E)-3-penten-1-ols, whereas nonterminal 3-alken-1-ols afford 4-methyl-branched derivs. with configurational inversion of the chain. Stereoselectivities were >99%. [on SciFinder (R)]
Title
Solvent-controlled additions of organotitanium reagents to olefinic double bonds
Published in
Tetrahedron Letters
Volume
26
Issue
37
Pages
4423-6
Date
1985
ISSN
0040-4039
Note
CAN 104:88082
23-7
Aliphatic Compounds
Inst. Chim. Org.,Lausanne,Switz.
Journal
written in English.
75-24-1; 917-54-4 Role: RCT (Reactant), RACT (Reactant or reagent) (methylation by, of homoallylic alcs., in presence of titanium tetrachloride); 7550-45-0 Role: USES (Uses) (methylation of homoallylic alcs. in presence of); 627-27-0; 763-32-6; 928-96-1; 928-97-2; 1632-68-4; 100420-53-9 Role: RCT (Reactant), RACT (Reactant or reagent) (methylation of, with titanium reagent); 459-88-1P; 764-37-4P; 1594-24-7P; 1708-98-1P; 21019-60-3P; 60322-66-9P; 63714-11-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
Record creation date
2006-03-03
