Diastereoselective synthesis of trans-2,3-dihydrofurans with pyridinium ylide assisted tandem reaction.
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.
Wang
Qi-Fang
QF
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
Hou
Hong
H
Hui
Li
L
Yan
Chao-Guo
CG
D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011726:Pyridinium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D005663:Furans; D011726:Pyridinium Compounds; C073812:2,3-dihydrofuran