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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, Universit della Calabria, I-87030 Arcavacata di Rende (CS), Italy, and Dipartimento di Chimica Organica A. Mangini, viale Risorgimento 4, I-40136 Bologna, Italy %procopio@unical.it

J. Org. Chem., 2002, 67 (25), pp 9093–9095

DOI: 10.1021/jo0260387

Publication Date (Web): November 15, 2002

†

Università della Calabria.

To whom correspondence should be addressed. Tel: +39 984 492077. Fax: +39 984 492055.

‡

Dipartimento di Chimica Organica “A. Mangini”.

Abstract

A new and chemoselective method for the cleavage of alkyl and cyclic acetals and ketals at room temperature in wet nitromethane by using catalytic cerium(III) trifluoromethane sulfonate is presented. The high yields, the observed selectivity, the very gentle reaction conditions, and the almost neutral pH make this procedure particularly attractive for multistep synthesis.

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Published In Issue December 13, 2002
Received June 11, 2002

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

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Related Content

A Simple and Efficient Chemoselective Method for the Catalytic Deprotection of Acetals and Ketals Using Bismuth Triflate

Ferric Chloride Hexahydrate: A Mild Hydrolytic Agent for the Deprotection of Acetals

Highly Efficient Deprotection of Acetals and Ketals under Neutral and Anhydrous Conditions Using (Trimethylsilyl)bis(fluorosulfuryl)imide

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