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Synlett 1996; 1996(1): 29-30
DOI: 10.1055/s-1996-5304
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Efficient Synthesis of Chiral N-Tosyl-3,4-Disubstituted Hexahydroazepins from D-(-)-Quinic Acid

Enrichetta Albertini, Achille Barco, Simonetta Benetti, Carmela De Risi, Gian P. Pollini* , Vinicio Zanirato
  • *Dipartimento di Scienze Farmaceutiche - Università di Ferrara - Via Fossato di Mortara 19, I-44100 Ferrara, Italy
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Publication History

Publication Date:
31 December 2000 (online)

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Basic alumina-promoted Beckmann rearrangement of the oxime tosylates of the cyclohexanone derivative 5, in turn obtained from the quinide 3 derived by acid-catalyzed reaction of D-(-)-quinic acid with benzaldehyde, gave rise to the formation of a mixture of chiral 4,5,6-trisubstituted hexahydroazepin-2-one regioisomers, which could be separated and further elaborated to N-tosyl-3,4-disubstituted hexahydroazepins, suitable precursors for balanol and its congeners.

D-(-)-Quinic Acid - Beckmann Rearrangement - Hexahydroazepin-2-ones

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