Tetrahedron

Mild and chemoselective catalytic deprotection of ketals and acetals using cerium (IV) ammonium nitrate

A Ates, A Gautier, B Leroy, JM Plancher, Y Quesnel…

Index: Ates, Ali; Gautier, Arnaud; Leroy, Bernard; Plancher, Jean-Marc; Quesnel, Yannick; Vanherck, Jean-Christophe; Marko, Istvan E. Tetrahedron, 2003 , vol. 59, # 45 p. 8989 - 8999

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Citation Number: 70

Abstract

Cerium (IV) ammonium nitrate (CAN) is a powerful, though mild, reagent for the efficient and selective removal of a range of ketals and acetals. This novel deprotection method requires only catalytic amounts of CAN and tolerates a variety of functional and protecting groups. Mechanistic insights suggest that the Ce (IV) salts act as unique Lewis acids and not as redox active species.

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