Metal-Free Deprotection of Terminal Acetonides by Using tert-Butyl Hydroperoxide in Aqueous Medium
Mahagundappa R. Maddani, Kandikere R. Prabhu*
*Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India, Email: prabhuorgchem.iisc.ernet.in
M. R. Maddani, K. R. Prabhu, Synlett, 2011, 821-825.
Aqueous tert-butyl hydroperoxide (70%) is an inexpensive reagent for the regioselective and chemoselective deprotection of terminal acetonide groups. Various acetonide derivatives furnish the corresponding deprotected diols in good yields, while a large number of acid labile protecting functional groups and other functional moieties were found to be unaffected under the conditions.
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deprotection, acetonides, tert-butyl hydroperoxide, chemoselectivity, protecting groups, diols