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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creator	Liu, Chun-Rong Zhu, Ben-Hu Zheng, Jun-Cheng Sun, Xiu-Li Xie, Zuowei Tang, Yong
description	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.
doi_str_mv	10.1039/c0cc02347g
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subjects	Catalysis Catalysts Cyclization Furans - chemical synthesis Furans - chemistry Imines Pyridines Pyridines - chemistry Pyrroles - chemical synthesis Pyrroles - chemistry Stereoisomerism Synthesis
title	Highly diastereroselective synthesis of dihydrofurans and dihydropyrroles via pyridine catalyzed formal [4+1] annulation
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