Divergent Chemo-, Regio-, and Diastereoselective Normal Electron-Demand Povarov-Type Reactions with alpha-Oxo-ketene Dienophiles - Aix-Marseille Université Access content directly
Journal Articles Organic Letters Year : 2014

Divergent Chemo-, Regio-, and Diastereoselective Normal Electron-Demand Povarov-Type Reactions with alpha-Oxo-ketene Dienophiles

Abstract

The reactions between electron-rich 2-aza- dienes and α-oxo-ketenes derived from the Wolff rearrange- ment of 2-diazocycloalkane-1,3-diones chemo- and regiose- lectively produced spiro hydropyrid-4-ones with good to excellent diastereoselectivities. These reactions are likely to proceed via a domino Wolff/Friedel−Crafts/intramolecular Mannich process. Prolonged domino sequences also allowed the expeditious preparation of a series of pyrazolopyridine and pyridopyrimidine heterocycles.
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hal-01133536 , version 1 (19-03-2015)

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J. Galvez, Juan-Carlos Castillo, J. Quiroga, M. Rajzmann, Jean Rodriguez, et al.. Divergent Chemo-, Regio-, and Diastereoselective Normal Electron-Demand Povarov-Type Reactions with alpha-Oxo-ketene Dienophiles. Organic Letters, 2014, 16, pp.4126-4129. ⟨10.1021/ol5018245⟩. ⟨hal-01133536⟩
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