MgI2-catalyzed halo aldol reaction: a practical approach to (E)-beta-iodovinyl-beta'-hydroxyketones.
A novel generation of 1-iodo-3-siloxy-1,3-butadienes has been developed by reacting trimethylsilyl iodide (TMS-I) with alpha, beta-unsaturated ketones in dichloromethane at 0 degrees C without the use of any catalyst. The halo aldol reaction of these butadiene intermediates with aldehydes was efficiently carried out by using magnesium iodide as the catalyst. Twelve beta-iodo-alpha,beta-unsaturated-beta'-hydroxyketones (halo aldols) have been synthesized under the new condition with excellent geometric selectivity and good chemical yields (>80% chemical yields for 11 examples).
Deparment of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409, USA.
Han-Xun
HX
Wei
Cody
C
Timmons
Mohamed Ali
MA
Farag
Paul W
PW
Pare
Guigen
G
Li
D002384:Catalysis; D007454:Iodides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D017616:Magnesium Compounds / Q000737:chemistry*; D015394:Molecular Structure
D007454:Iodides; D007659:Ketones; D017616:Magnesium Compounds; C510205:magnesium iodide