Wei Han-Xun, Timmons Cody, Farag Mohamed Ali, Pare Paul W, Li Guigen
Deparment of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409, USA.
Org Biomol Chem. 2004 Oct 21;2(20):2893-6. doi: 10.1039/B409056J. Epub 2004 Sep 27.
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).
通过在0℃下于二氯甲烷中使三甲基碘化硅（TMS-I）与α，β-不饱和酮反应，在不使用任何催化剂的情况下，开发出了新一代的1-碘-3-硅氧基-1,3-丁二烯。通过使用碘化镁作为催化剂，这些丁二烯中间体与醛的卤代羟醛反应得以高效进行。在新条件下合成了12种β-碘-α，β-不饱和-β'-羟基酮（卤代羟醛），具有出色的几何选择性和良好的化学产率（11个实例的化学产率>80%）。
