MgI2-catalyzed halo aldol reaction: a practical approach to (E)-beta-iodovinyl-beta'-hydroxyketones |
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Authors: | Wei Han-Xun Timmons Cody Farag Mohamed Ali Pare Paul W Li Guigen |
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Institution: | Deparment of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409, USA. |
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Abstract: | 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). |
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