Low-Temperature n-Butyllithium-Induced Rearrangement of Allyl 1,1-Dichlorovinyl Ethers

Upon treatment with n-BuLi at low temperatures, a variety of allyl 1,1-dichlorovinyl ethers 2 undergo rearrangement to furnish γ,δ-unsaturated esters 3 after alcohol addition. Compounds containing quaternary centers (3e:  R1 = H, R2, R3 = −(CH2)5−; 3f:  R1 = H, R2 = CH3, R3 = (CH2)2CH(CH3)2) may be...

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Bibliographic Details
Published in:Organic letters 2006-02, Vol.8 (3), p.451-454
Main Authors: Christopher, Aaron, Brandes, Dahniel, Kelly, Stephen, Minehan, Thomas
Format: Article
Language:English
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Summary:Upon treatment with n-BuLi at low temperatures, a variety of allyl 1,1-dichlorovinyl ethers 2 undergo rearrangement to furnish γ,δ-unsaturated esters 3 after alcohol addition. Compounds containing quaternary centers (3e:  R1 = H, R2, R3 = −(CH2)5−; 3f:  R1 = H, R2 = CH3, R3 = (CH2)2CH(CH3)2) 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 Δ2,3-β-C-glycosides and α,β-disubstituted lactones.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052685j