Basic alumina-promoted Beckmann rearrangement of the oxime tosylates of the cyclohexanone derivative, in turn obtained from the quinide 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 hexahydroazepines, suitable precursors for balanol and its congeners.
Efficient synthesis of chiral N-tosyl-3,4-disubstituted hexahydroazepines from D-(-)-quinic acid
BARCO, Achille;BENETTI, Simonetta;DE RISI, Carmela;POLLINI, Gian Piero;ZANIRATO, Vinicio
1996
Abstract
Basic alumina-promoted Beckmann rearrangement of the oxime tosylates of the cyclohexanone derivative, in turn obtained from the quinide 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 hexahydroazepines, suitable precursors for balanol and its congeners.File in questo prodotto:
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