MgI2-catalyzed halo aldol reaction: A practical approach to (E)-β-iodovinyl-β′-hydroxyketones

Han Xun Wei, Cody Timmons, Mohamed Ali Farag, Paul W. Paré, Guigen Li

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

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 languageEnglish
Pages (from-to)2893-2896
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume2
Issue number20
DOIs
StatePublished - Oct 21 2004

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