Facile synthesis of enantiomerically pure 2- and 2,3-disubstituted furans catalysed by mixed Lewis acids: an easy route to 3-iodofurans and 3-(hydroxymethyl)furans.
Simple and efficient syntheses, catalysed by a mixed Lewis acid system (ZrCl(4)/ZnI(2)), of enantiomerically pure 2- and 2,3-disubstituted furan derivatives--including important synthons such as 3-iodofuran and 3-(hydroxymethyl)furan derivatives--from commercially available 3,4,6-tri-O-acetyl-D-glucal are described. The transformation is achieved through a synergistic interaction between ZrCl(4) and ZnI(2) in catalytic amounts.
Saquib
Mohammad
M
Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow-226001, India.
Husain
Irfan
I
Kumar
Brijesh
B
Shaw
Arun K
AK
D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D017967:Zinc Compounds / Q000737:chemistry
D002712:Chlorides; D005663:Furans; D007454:Iodides; D017967:Zinc Compounds; C029770:zinc iodide; C016837:zinc chloride