Oxidation of Vicinal Diols to α‐Hydroxy Ketones with H(2)O(2) and a Simple Manganese Catalyst

α‐Hydroxy ketones are valuable synthons in organic chemistry. Here we show that oxidation of vic‐diols to α‐hydroxy ketones with H(2)O(2) can be achieved with an in situ prepared catalyst based on manganese salts and pyridine‐2‐carboxylic acid. Furthermore the same catalyst is effective in alkene ep...

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Detalles Bibliográficos
Autores principales: Mecozzi, Francesco, Dong, Jia Jia, Saisaha, Pattama, Browne, Wesley R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5767754/
https://www.ncbi.nlm.nih.gov/pubmed/29398954
http://dx.doi.org/10.1002/ejoc.201701314
Descripción
Sumario:α‐Hydroxy ketones are valuable synthons in organic chemistry. Here we show that oxidation of vic‐diols to α‐hydroxy ketones with H(2)O(2) can be achieved with an in situ prepared catalyst based on manganese salts and pyridine‐2‐carboxylic acid. Furthermore the same catalyst is effective in alkene epoxidation, and it is shown that alkene oxidation with the Mn(II) catalyst and H(2)O(2) followed by Lewis acid ring opening of the epoxide and subsequent oxidation of the alkene to α‐hydroxy ketones can be achieved under mild (ambient) conditions.

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