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A simple and efficient chemoselective method for the catalytic deprotection of acetals and ketals using bismuth
Marc D Carrigan1, Dusan Sarapa, Russell C Smith
1Department of Chemistry, Illinois Wesleyan University, Bloomington, Illinois 61701, USA.
The Journal of Organic Chemistry
|February 22, 2002
Abstract:
Bismuth triflate is a highly efficient catalyst (0.1-1 mol %) for the deprotection of acetals and ketals. The procedure is very facile and selective for acetals derived from ketones and conjugated aldehydes. tert-Butyldimethylsilyl ethers are stable to the reaction conditions. The highly catalytic nature of bismuth triflate and the use of a relatively nontoxic solvent system (THF/H(2)O) make this procedure particularly attractive for large-scale synthesis.