☆ 4.8 Article

Isomerization of Allyl Ethers Initiated by Lithium Diisopropylamide

ORGANIC LETTERS (2010)

Journal

ORGANIC LETTERS

Volume 12, Issue 23, Pages 5378-5381

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/ol102029u

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Categories

Chemistry, Organic

Funding

NSF [0718275]
Direct For Mathematical & Physical Scien
Division Of Chemistry [0718275] Funding Source: National Science Foundation

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Abstract

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.

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