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Synlett 2011(14): 2048-2052
DOI: 10.1055/s-0030-1260980
DOI: 10.1055/s-0030-1260980
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New YorkOne-Pot Bi(OTf)3-Catalyzed Oxidative Deprotection of tert-Butyldimethyl Silyl Ethers with TEMPO and Co-Oxidants
Weitere Informationen
Received
7 April 2011
Publikationsdatum:
03. August 2011 (online)
Publikationsverlauf
Publikationsdatum:
03. August 2011 (online)
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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References and Notes
In the presence of PhIO/TEMPO system, diacetone galactose gave mainly polar products.