Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 8, Pages 1719-1724Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201400093
Keywords
asymmetric synthesis; aza-Diels-Alder reaction; chiral phosphoric acid; organocatalysis; Povarov reaction
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Funding
- ICSN
- CNRS
- Astrazeneca
- AZ
- MESR, University of Paris XI
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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.
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