Volume 31, Issue 5
Preparative Organic Chemistry
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ChemInform Abstract: Cerium(IV)-Catalyzed Deprotection of Acetals and Ketals under Mildly Basic Conditions.

Istvan E. Marko

Istvan E. Marko

Lab. Chim. Org., Univ. Cathol. Louvain, B-1348 Louvain-la-Neuve, Belg.

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Ali Ates

Ali Ates

Lab. Chim. Org., Univ. Cathol. Louvain, B-1348 Louvain-la-Neuve, Belg.

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Arnaud Gautier

Arnaud Gautier

Lab. Chim. Org., Univ. Cathol. Louvain, B-1348 Louvain-la-Neuve, Belg.

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Bernard Leroy

Bernard Leroy

Lab. Chim. Org., Univ. Cathol. Louvain, B-1348 Louvain-la-Neuve, Belg.

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Jean-Marc Plancher

Jean-Marc Plancher

Lab. Chim. Org., Univ. Cathol. Louvain, B-1348 Louvain-la-Neuve, Belg.

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Yannick Quesnel

Yannick Quesnel

Lab. Chim. Org., Univ. Cathol. Louvain, B-1348 Louvain-la-Neuve, Belg.

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Jean-Christophe Vanherck

Jean-Christophe Vanherck

Lab. Chim. Org., Univ. Cathol. Louvain, B-1348 Louvain-la-Neuve, Belg.

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First published: 11 June 2010

Abstract

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ChemInform Abstract

Application of a novel highly efficient deprotection method with catalytic amounts of cerium ammonium nitrate under mildly basic conditions (borate—HCl buffer solution) to a series of acetals and ketals shows that the cerium catalyst is highly sensitive to steric hindrance in the ketal protecting group and/or in its immediate vicinity, e.g. prolonged reaction time required for deprotection of decalone derivative (VII) and total inertness of pinacol-derived ketal (IX) under these reaction conditions.

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