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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, Email: vateleuniv-lyon1.fr

B. Barnych, J.-M. Vatèle, Synlett, 2011, 2048-2052.

DOI: 10.1055/s-0030-1260980 (free Supporting Information)


Abstract

A sequential one-pot synthesis for the oxidation of primary and secondary tert-butyldimethylsilyl (TBDMS) ethers, using the presence of PhIO or PhI(OAc)2 and catalytic amounts of metal triflates and TEMPO in THF or acetonitrile tolerates acid-sensitive protecting groups and leaves tert-butyldiphenylsilyl ethers and phenolic TBDMS groups untouched.


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Yb(OTf)3-Catalyzed Oxidation of Alcohols with Iodosylbenzene Mediated by TEMPO

J.-M. Vatèle, Synlett, 2006, 2055-2058.


Key Words

TBDMS-protected hydroxyl groups, aldehydes, ketones, TEMPO, Iodosylbenzene, bismuth(III) triflate


ID: J60-Y2011-2490