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Simple and Efficient Chemoselective Mild Deprotection of Acetals and Ketals Using Cerium(III) Triflate

Renato Dalpozzo, Antonio De Nino, Loredana Maiuolo, Antonio Procopio,* Antonio Tagarelli, Giovanni Sindona and Giuseppe Bartoli

*Dipartimento di Chimica, UniversitÓ della Calabria, I-87030 Arcavacata di Rende (CS), Italy, and Dipartimento di Chimica Organica "A. Mangini", viale Risorgimento 4, I-40136 Bologna, Italy, Email: procopiounical.it

R. Dalpozzo, A. De Nino, L. Maiuolo, A. Procopio, A. Tagarelli, G. Sindona, G. Bartoli, J. Org. Chem., 2002, 67, 9093-9095.

DOI: 10.1021/jo0260387


Abstract

A chemoselective method for the cleavage of acetals and ketals at room temperature in wet nitromethane by using catalytic cerium(III) triflate at almost neutral pH is presented. High yields and selectivity make this procedure particularly attractive for multistep synthesis.

see article for more example



Er(OTf)3 as a Mild Cleaving Agents for Acetals and Ketals

R. Dalpozzo, A. De Nino, L. Maiuolo, M. Nardi, A. Procopio, A. Tagarelli, Synthesis, 2004, 496-498.


Key Words

cerium(III) triflate, Lewis acid catalyst, cleavage (acetals, ketals), 1,3-dioxolanes, dimethyl acetals


ID: J42-Y2002-920