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Diastereoselective Synthesis of trans-2,3-Dihydrofurans with Pyridinium Ylide Assisted Tandem Reaction

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journal contribution
posted on 02.10.2009, 00:00 by Qi-Fang Wang, Hong Hou, Li Hui, Chao-Guo Yan
An efficient synthetic procedure for the preparation of fused 2,3-dihydrofuran derivatives was developed with the assistance of pyridinium ylide. A sequential one-pot, two-step tandem reaction starting from pyridine, aromatic aldehyde, dimedone, or 4-hydroxycoumarin and α-phenacyl bromide or p-nitrobenzyl bromide with triethylamine as catalyst proceeded smoothly in acetonitrile. 1H NMR spectroscopy and single-crystal analysis demonstrated that the obtained 2,3-dihydrofurans are trans isomers.