EFFICIENT SYNTHESIS OF CHIRAL N-TOSYL-3,4-DISUBSTITUTED HEXAHYDROAZEPINES FROM D-(-)-QUINIC ACID

Authors
ALBERTINI E BARCO A BENETTI S DERISI C POLLINI GP ZANIRATO V
Citation
E. Albertini et al., EFFICIENT SYNTHESIS OF CHIRAL N-TOSYL-3,4-DISUBSTITUTED HEXAHYDROAZEPINES FROM D-(-)-QUINIC ACID, Synlett, (1), 1996, pp. 29
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
1
Year of publication
1996
Database
ISI
SICI code
0936-5214(1996):1<29:ESOCNH>2.0.ZU;2-G
Abstract
Basic alumina-promoted Beckmann rearrangement of the oxime tosylates o f the cyclohexanone derivative 5, in turn obtained from the quinide 3 derived by acid-catalyzed reaction of D-(-)-quinic acid with benzaldeh yde, gave rise to the formation of a mixture of chiral 4,5,6-trisubsti tuted hexahydroazepin-2-one regioisomers, which could be separated and further elaborated to N-tosyl-3,3-disubsituted hexahydroazepines, sui table precursors for balanol and its congeners.