H₈-BINOL chiral imidodiphosphoric acid catalyzed highly enantioselective aza-Friedel-Crafts reactions of pyrroles and enamides/imines

H₈-BINOL chiral imidodiphosphoric acid catalyzed highly enantioselective aza-Friedel-Crafts reactions of pyrroles and enamides/imines

The first enantioselective aza-Friedel-Crafts reaction between pyrroles and enamides has been achieved by using a novel H8-BINOL-type imidodiphosphoric acid catalyst. This methodology was also applied to the highly enantioselective aza-Friedel-Crafts reaction between pyrroles and imines. The catalys...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2015-05, Vol.51 (38), p.8054-8057
Hauptverfasser: Wu, Kun, Zhuo, Ming-Hua, Sha, Di, Fan, Yan-Sen, An, Dong, Jiang, Yi-Jun, Zhang, Suoqin
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
Amines - chemical synthesis
Amines - chemistry
Catalysis
Diphosphonates - chemistry
Imines - chemistry
Molecular Structure
Naphthols - chemistry
Pyrroles - chemistry
Stereoisomerism
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Zusammenfassung:The first enantioselective aza-Friedel-Crafts reaction between pyrroles and enamides has been achieved by using a novel H8-BINOL-type imidodiphosphoric acid catalyst. This methodology was also applied to the highly enantioselective aza-Friedel-Crafts reaction between pyrroles and imines. The catalyst loadings in these two reactions are low (0.3-2 mol%). Both processes are amenable to gram scales.
ISSN:1364-548X
DOI:10.1039/c5cc00685f