Issue 5, 2000

Carbohydrate α-oxoketene N,O-ketals in the synthesis of dihydroquinolines

Abstract

The carbohydrate nitro enone 1 was found to react with amines to give α-ketene ketals; the formation of carbohydrate azo derivatives could be suppressed by addition of an electron-rich aniline quenching agent. Upon reaction with benzaldehyde in the presence of trifluoroacetic acid, the α-oxoketene ketals afforded dihydroquinolines in a cyclization reaction forming two new carbon–carbon bonds. For the dihydroquinoline 18 the newly formed stereocenter was ascertained by X-ray crystallography. The two-step reaction could be carried out as one multicomponent reaction. Electron-poor anilines led to Hantzsch-type products incorporating two enaminone molecules; the crystal structure of representative 30 is reported.

Supplementary files

Article information

Article type
Paper
Submitted
04 Nov 1999
Accepted
01 Dec 1999
First published
17 Feb 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 753-762

Carbohydrate α-oxoketene N,O-ketals in the synthesis of dihydroquinolines

G. Scheffler, F. Montavon, M. Hennig and H. P. Wessel, J. Chem. Soc., Perkin Trans. 1, 2000, 753 DOI: 10.1039/A908806G

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