Journal of Organic Chemistry 2002-02-08

A simple and efficient chemoselective method for the catalytic deprotection of acetals and ketals using bismuth triflate.

Marc D Carrigan, Dusan Sarapa, Russell C Smith, Laura C Wieland, Ram S Mohan

Index: J. Org. Chem. 67(3) , 1027-30, (2002)

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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.