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Oxidation of Amino Diols Mediated by Homogeneous and Heterogeneous TEMPO
Author(s) -
Testa Maria Luisa,
Ciriminna Rosaria,
Hajji Chakib,
Zaballos Garcia Elena,
Ciclosi Marco,
Sepulveda Arques Jose,
Pagliaro Mario
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200303239
Subject(s) - chemistry , homogeneous , homogeneous catalysis , combinatorial chemistry , organic chemistry , catalysis , physics , thermodynamics
Abstract The conversion of amino diols to aminohydroxy acids by oxidation of the primary hydroxy group mediated by homogeneous and heterogeneous TEMPO (2,2,6,6‐tetramethylpiperidine 1‐oxyl radical) is reported. The synthesis uses NaOCl as primary oxidant and TEMPO, either dissolved in the homogeneous phase or entrapped in a sol‐gel matrix, as catalytic mediator. Homogeneous TEMPO is suitable for the oxidation of aliphatic methylamino diols, while the hybrid organic‐inorganic silica sol‐gel catalysts are more selective mediators for the oxidation of benzylic amino diols like the potent antibiotic chloramphenicol which, under homogeneous conditions, are unselectively oxidized to benzoic acids.