Abstract
A novel generation of 1-iodo-3-siloxy-1,3-butadienes has been developed by reacting trimethylsilyl iodide (TMS-I) with α,β-unsaturated ketones in dichloromethane at 0°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 β-iodo-α, β-unsaturated-β′-hydroxyketones (halo aldols) have been synthesized under the new condition with excellent geometric selectivity and good chemical yields (>80% chemical yields for 11 examples).
Original language | English |
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Pages (from-to) | 2893-2896 |
Number of pages | 4 |
Journal | Organic and Biomolecular Chemistry |
Volume | 2 |
Issue number | 20 |
DOIs | |
State | Published - Oct 21 2004 |