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1 article(s) from Górecki, Łukasz

Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination

Łukasz Górecki,
Artur Mucha and
Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 883–889, doi:10.3762/bjoc.10.85

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Scheme 1: Quinine (1) and O-9-t-butylcarbamoylquinine (2) as the substrates for oxidation of the C9 hydroxy a...

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Scheme 2: Oxidation of the vinyl group of 9-O-tert-butylcarbamoylquinine to homologous aldehydes.

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Scheme 3: Addition of diethyl phosphite to aldehydes obtained in oxidation of the vinyl group.

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Scheme 4: Oxidation of quinine to quininone and quinidinone and addition of phosphites to the ketones yieldin...

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Scheme 5: Spectroscopic features that confirmed the structure of the phosphate ester product of rearrangement...

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Scheme 6: Tentative mechanism of the phosphonate–phosphate rearrangement associated with tandem quinuclidine ...

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Published 17 Apr 2014

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