ORGN 955 |
| Upon treatment with n-butyllithium at -78°C, a variety of allyl-1,1-dichlorovinyl ethers undergo rapid sigmatropic rearrangement to furnish γ,δ-unsaturated esters, thioesters, or amides after alcohol, thiol or amine addition. Compounds containing quaternary centers may be formed in high yield and under mild conditions utilizing this protocol. The reaction is stereospecific and may be applied to the preparation of β-C-glycosides and α,β-disubstituted lactones. Evidence delineating a possible mechanistic pathway for this reaction will be presented. |
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New Reactions and Methodology
1:00 PM-5:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 133, Oral
Division of Organic Chemistry |