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  • 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.

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.

Chemistry (Weinheim an der Bergstrasse, Germany) (2009-05-07)
Mohammad Saquib, Irfan Husain, Brijesh Kumar, Arun K Shaw
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Zinc iodide, ≥98%
Sigma-Aldrich
Zinc iodide, anhydrous, powder, 99.999% trace metals basis
Sigma-Aldrich
Zinc iodide, ≥99.99% trace metals basis
Sigma-Aldrich
Zinc iodide, purum p.a., ≥98.0% (AT)