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.


Published in:
Advanced Synthesis & Catalysis, 356, 8, 1719-1724
Year:
2014
Publisher:
Weinheim, Wiley-Blackwell
ISSN:
1615-4150
Keywords:
Laboratories:




 Record created 2014-06-08, last modified 2018-03-17


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