Efficient Synthesis of Chiral N-Tosyl-3,4-Disubstituted Hexahydroazepins from D-(-)-Quinic Acid

Publisher Website
Google Scholar
Abstract
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.

This publication has 0 references indexed in Scilit: