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

作者:Wang Qi Fang; Hou Hong; Hui Li; Yan Chao Guo*
来源:Journal of Organic Chemistry, 2009, 74(19): 7403-7406.
DOI:10.1021/jo901379h

摘要

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 alpha-phenacyl bromide or p-nitrobenzyl bromide with triethylamine as catalyst proceeded smoothly in acetonitrile. (1)H NMR spectroscopy and single-crystal analysis demonstrated that the obtained 2,3-dihydrofurans are trans isomers.