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Synlett 2011(14): 2048-2052  
DOI: 10.1055/s-0030-1260980
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Bi(OTf)3-Catalyzed Oxidative Deprotection of tert-Butyldimethyl Silyl Ethers with TEMPO and Co-Oxidants

Bogdan Barnych, Jean-Michel Vatèle*
Université Lyon 1, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), UMR 5246 CNRS, Equipe SURCOOF, Bât. Raulin, 43, Blvd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France
e-Mail: vatele@univ-lyon1.fr;
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Publication History

Received 7 April 2011
Publication Date:
03 August 2011 (online)

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Abstract

A sequential one-pot synthesis for the oxidation of primary and secondary tert-butyldimethylsilyl (TBDMS) ethers, using catalytic amounts of metal triflates and TEMPO in combination with PhIO or PhI(OAc)2 in THF or acetonitrile, is described. Acid-sensitive protecting groups such as methylidene, isopropylidene, acetals, and Boc are unaffected under the reaction conditions. Another feature of this procedure is its high selectivity for TBDMS ethers over tert-butyldiphenylsilyl ethers and of aliphatic TBDMS groups over phenolic TBDMS groups.

Key words

bismuth(III) triflate - carbonyl compounds - oxidation - silyl ethers - TEMPO

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16

In the presence of PhIO/TEMPO system, diacetone galactose gave mainly polar products.