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Mild Oxidative One-Pot Allyl Group Cleavage

Pavel I. Kitov and David R. Bundle*

*Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2, Email:

P. I. Kitov, D. R. Bundle, Org. Lett., 2001, 3, 2835-2838.

DOI: 10.1021/ol016278t


A new one-pot method is described for the removal of O- and N-allyl protecting groups under oxidative conditions at near neutral pH. The allyl group undergoes hydroxylation and subsequent periodate scission of the vicinal diol. Repetition of this reaction sequence on the enol tautomer of the aldehyde intermediate releases the deprotected functional group.

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proposed mechanism

Key Words

Allyl Ethers, Deprotection (Amines, Alcohols), Osmium tetroxide, NMO, Sodium periodate

ID: J54-Y2004-720