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Isomerization of Allyl Ethers Initiated by Lithium Diisopropylamide

Chicheung Su and Paul G. Williard*

*Department of Chemistry, Brown University, Providence, Rhode Island 02912, United States, Email: pgwbrown.edu

C. Su, P. G. Williard, Org. Lett., 2010, 12, 5378-5381.

DOI: 10.1021/ol102029u (free Supporting Information)


Abstract

Lithium diisopropylamide (LDA) promotes virtually quantitative conversion of allylic ethers to (Z)-propenyl ethers with very high stereoselectivity in THF at room temperature. The reaction time for the conversion increases with more sterically hindered allylic ethers.

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Key Words

Isomerizations, Silyl Enol Ethers


ID: J54-Y2010-3360