Pinacol coupling reaction of beta-halo-alpha,beta-unsaturated aldehydes promoted by TiI4.
The pinacol reaction of beta-halogenated alpha,beta-unsaturated aldehydes was promoted by titanium tetraiodide to give coupling products in good yields with high dl-selectivity. Subsequent reduction with H(2)/Pd-C gave saturated vic-diols in good yields. Heck coupling reaction enabled the displacement of halogens with vinyl groups without the loss of stereochemical integrities. [reaction: see text]
Shimizu
Makoto
M
Department of Chemistry for Materials, Mie University, Tsu, Mie 514-8507, Japan. mshimizu@chem.mie-u.ac.jp
Goto
Hiroshi
H
Hayakawa
Ryuuichirou
R
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D002074:Butanones; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis; D007202:Indicators and Reagents; D007454:Iodides / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation
D000447:Aldehydes; D002074:Butanones; D017320:HIV Protease Inhibitors; D007202:Indicators and Reagents; D007454:Iodides; C084935:pinacolone