Beilstein J. Org. Chem.2014,10, 883–889, doi:10.3762/bjoc.10.85
skeleton and a phosphorus atom. For the C9 ketones a phosphonate–phosphate rearrangement, associated with a tandem elimination of the piperidine fragment, was evidenced.
Keywords: carbonyl derivatives; dialkyl phosphite addition; organophosporus; phosphonate–phosphate rearrangement; quinine oxidation
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Graphical Abstract
Scheme 1:
Quinine (1) and O-9-t-butylcarbamoylquinine (2) as the substrates for oxidation of the C9 hydroxy a...