High yield protection of alcohols, including tertiary and base sensitive alcohols, as benzhydryl ethers by heating with diphenyldiazomethane in the absence of any other reagent

A protecting group that can be introduced efficiently without the need for any acid or base catalysis and which is not prone to acid or base catalysed migration is a significant advantage for many syntheses. Benzhydryl [diphenylmethyl] ethers of sugar lactones are formed in high yield under neutral...

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Bibliographic Details
Published in:Tetrahedron letters 2008-03, Vol.49 (14), p.2196-2199
Main Authors: Best, Daniel, Jenkinson, Sarah F., Rule, Sebastian D., Higham, Rosemary, Mercer, Thomas B., Newell, Richard J., Weymouth-Wilson, Alexander C., Fleet, George W.J., Petursson, Sigthor
Format: Article
Language:English
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Summary:A protecting group that can be introduced efficiently without the need for any acid or base catalysis and which is not prone to acid or base catalysed migration is a significant advantage for many syntheses. Benzhydryl [diphenylmethyl] ethers of sugar lactones are formed in high yield under neutral conditions when the corresponding alcohol is heated with diphenyldiazomethane in an inert solvent such as acetonitrile or toluene; this allows the easy protection of base sensitive and highly hindered tertiary alcohols in the absence of any other reagents.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.02.042