Organic Chemistry Portal



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:

M. R. Maddani, K. R. Prabhu, Synlett, 2011, 821-825.

DOI: 10.1055/s-0030-1259917


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.

see article for more examples

Key Words

deprotection, acetonides, tert-butyl hydroperoxide, chemoselectivity, protecting groups, diols

ID: J60-Y2011-0860