ORGN 22 |
| A method for the synthesis of diisopinocampheylalkylboranes via indium metal and the corresponding allyl or propargyl bromide will be presented. Current methodologies used to prepare homoallylic alcohols utilize allylboron reagents which are prepared from the corresponding allylmagnesium or allyllithium precursors. A drawback of this methodology is that only unfunctionalized allylic starting materials can be used since organomagnesium and organolithium reagents are reactive toward many functional groups. We have found a simple method for the synthesis of highly functionalized allylboron intermediates using allylindium compounds as a means of circumventing this limitation. Consequently, highly functionalized chiral molecules can be easily assembled by the addition of a carbonyl to a functionalized allyl halide in the presence of indium and B-chlorodiisopinocampheylborane.
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Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, August 19, 2007 BCEC -- 254 A/B, Oral
Division of Organic Chemistry |
