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: dave.bundle
ualberta.ca
P. I. Kitov, D. R. Bundle, Org. Lett., 2001, 3, 2835-2838.
DOI: 10.1021/ol016278t
Abstract
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.
see article for more examples
proposed mechanism
Key Words
Allyl Ethers, Deprotection (Amines, Alcohols), Osmium tetroxide, NMO, Sodium periodate
ID: J54-Y2004-720
