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ChemInform Abstract: A Multicomponent One-Pot Reaction Integrating a Bisfunctional Carbohydrate Derivative.

✍ Scribed by Goetz Scheffler; Michael Justus; Andrea Vasellla; Hans Peter Wessel

Publisher
John Wiley and Sons
Year
2010
Weight
32 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

A Multicomponent One-Pot Reaction Integrating a Bisfunctional Carbohydrate Derivative.

-Treatment of enantiopure carbohydrate derived 2-nitroenone (I) with anilines affords ketene-N,O-acetals [cf. (III)] which smoothly react with benzaldehyde to furnish hydroxylated derivatives of pharmacologically interesting dihydropyridine and -quinoline derivatives [cf. (V), (VIII)]. The procedure can be accomplished in a one-pot reaction.

The yields in the one-pot procedure are lower than in the sequential reactions with intermediate purification, however, the stereoselectivities are significantly improved, in general.

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