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research article
Chiral Phosphoric Acid-Catalyzed Enantioselective Three- Component Aza-Diels-Alder Reactions of Aminopyrroles and Aminopyrazoles
A highly stereoselective three-component Povarov reaction, catalyzed by (R)- and (S)-BINOL hydrogen phosphate, was achieved for the first time with aminopyrroles and aminopyrazoles as 2-azadiene precursors. A variety of aldehydes, enecarbamates, amino-substituted azines participated in the reaction to afford the tetrahydropyrrolopyridines and tetrahydropyrazolopyridines in good yields with excellent diatereo- and enantioselectivities. A stereochemical model is proposed to account for the observed absolute stereochemistry.
Type
research article
Web of Science ID
WOS:000337584200006
Authors
Brioche, Julien
•
Courant, Thibaut
•
Alcaraz, Lilian
•
Stocks, Michael
•
Furber, Mark
•
•
Masson, Géraldine
Publication date
2014
Publisher
Published in
Volume
356
Issue
8
Start page
1719
End page
1724
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
June 8, 2014
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