Highly diastereroselective synthesis of dihydrofurans and dihydropyrroles via pyridine catalyzed formal [4+1] annulation

Highly diastereroselective synthesis of dihydrofurans and dihydropyrroles via pyridine catalyzed formal [4+1] annulation

A pyridine-catalyzed ylide cyclization affording dihydrofurans and dihydropyrroles has been developed. In the presence of a catalytic amount of pyridine and Fe(Tcpp)Cl, α-ylidene-β-diketones and α,β-unsaturated imines react with diazoacetates providing dihydrofurans and dihydropyrroles respectively,...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2011-01, Vol.47 (4), p.1342-1344
Hauptverfasser: Liu, Chun-Rong, Zhu, Ben-Hu, Zheng, Jun-Cheng, Sun, Xiu-Li, Xie, Zuowei, Tang, Yong
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Catalysts
Cyclization
Furans - chemical synthesis
Furans - chemistry
Imines
Pyridines
Pyridines - chemistry
Pyrroles - chemical synthesis
Pyrroles - chemistry
Stereoisomerism
Synthesis
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Beschreibung
Zusammenfassung:A pyridine-catalyzed ylide cyclization affording dihydrofurans and dihydropyrroles has been developed. In the presence of a catalytic amount of pyridine and Fe(Tcpp)Cl, α-ylidene-β-diketones and α,β-unsaturated imines react with diazoacetates providing dihydrofurans and dihydropyrroles respectively, in up to 96% yield with high diastereoselectivities.
ISSN:1359-7345
1364-548X
DOI:10.1039/c0cc02347g