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

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 sugg...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 59; no. 45; pp. 8989 - 8999
Main Authors Ates, Ali, Gautier, Arnaud, Leroy, Bernard, Plancher, Jean-Marc, Quesnel, Yannick, Vanherck, Jean-Christophe, Markó, István E
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 03.11.2003
Elsevier
Subjects
acetals
catalysis
cerium and compounds
Chemistry
Chemistry, Organic
deprotection
ketals
Physical Sciences
Science & Technology
deprotection
cerium and compounds
catalysis
ketals
acetals
REAGENT
OXIDATION
CONVERGENT TOTAL-SYNTHESIS
SILICA-GEL
CYCLIC ACETALS
TERT-BUTYLDIMETHYLSILYL
EFFICIENT DEPROTECTION
ETHERS
ORGANIC-COMPOUNDS
SELECTIVE CLEAVAGE
Online AccessGet full text
ISSN0040-4020
1464-5416
DOI10.1016/j.tet.2003.03.002

Cover

More Information
Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2003.03.002