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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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New protecting groups for 1,2-diols (boc- and moc-ethylidene). Cleavage of acetals with bases.

[reaction: see text] 1,2-Diols react at rt with alkyl propynoates, in the presence of 4-dimethylaminopyridine, to give cyclic acetals which are quite stable to acid-catalyzed hydrolysis or methanolysis. 1,3-Diols and 1, 4-diols do not form acetals with alkyl propynoates under the same conditions. Deprotection is accomplished with bases (via elimination and addition/elimination steps).[1]

References

  1. New protecting groups for 1,2-diols (boc- and moc-ethylidene). Cleavage of acetals with bases. Ariza, X., Costa, A.M., Faja, M., Pineda, O., Vilarrasa, J. Org. Lett. (2000) [Pubmed]
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