Oxoammonium salts. Part 8: Oxidations in base: oxidation of O-1 unprotected monosaccharides to lactones using 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate
2001; Elsevier BV; Volume: 42; Issue: 50 Linguagem: Inglês
10.1016/s0040-4039(01)01950-5
ISSN1873-3581
AutoresNabyl Merbouh, James M. Bobbitt, Christian Brückner,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoAbstract The oxidant, 4-acetylamino-2,2,6,6-tetramethylpiperidine-oxoammonium tetrafluoroborate in pyridine/CH 2 Cl 2 , is reported to be an excellent reagent for the conversion of hemiacetals to lactones. Specifically, the conversion of 1-O unprotected sugars to their corresponding aldonolactones is achieved in high yields. The basic reaction conditions partially overcome some disadvantages reported for oxoammonium-type oxidants, namely the inability to run the reaction in the presence of acid-labile groups and in the presence of β-oxygens.
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