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Isomerization of allyl ethers initiated by lithium diisopropylamide.
Department of Chemistry, Brown University, Providence, Rhode Island 02912, USA.
Organic letters 2010 Dec 3Sizes of these terms reflect their relevance to your search.
Lithium diisopropylamide (LDA) promotes virtually quantitative conversion of allylic ethers to (Z)-propenyl ethers. It was discovered that allylic ethers can be isomerized efficiently with very high stereoselectivity to (Z)-propenyl ethers by LDA in THF at room temperature. The reaction time for the conversion increases with more sterically hindered allylic ethers. Different amides were also compared with LDA for their ability to effect this isomerization.
Citation
Chicheung Su, Paul G Williard. Isomerization of allyl ethers initiated by lithium diisopropylamide. Organic letters. 2010 Dec 3;12(23):5378-81
PMID: 21053981
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