Synlett 2018; 29(17): 2298-2300
DOI: 10.1055/s-0037-1610292
letter
© Georg Thieme Verlag Stuttgart · New York

Brønsted Acid Mediated Direct α-Hydroxylation of Cyclic α-Branched Ketones

Grigory A. Shevchenko
,
Stefanie Dehn
,
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany   eMail: list@kofo.mpg.de
› Institutsangaben
This work was partially supported by Max Planck Society and the DFG
Weitere Informationen

Publikationsverlauf

Received: 21. August 2018

Accepted after revision: 02. September 2018

Publikationsdatum:
26. September 2018 (online)


Abstract

We report a Brønsted acid mediated direct α-hydroxylation of cyclic α-branched ketones via a tandem aminoxylation/N–O bond-cleavage process. Nitrosobenzene is used as the oxidant and subsequently promotes the liberation of the free alcohol. The desired products could be isolated in moderate to good yields at a maximum tested scale of 10 mmol. Derivatizations of the obtained products are presented.

Supporting Information