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

✍ Scribed by Mohammad Saquib; Irfan Husain; Brijesh Kumar; Arun K. Shaw

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 283 KB
• Volume: 15
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200900007

✦ Synopsis

Abstract

Enantiopure furan synthesis: A synthesis, catalysed by mixed Lewis acids (ZrCl~4~/ZnI~2~), of enantiomerically pure 2‐ and 2,3‐disubstituted furan derivatives, including 3‐iodofuran and 3‐ (hydroxymethyl)furan derivatives, in good to very good yields from commercially available 3,4,6‐tri‐O‐acetyl‐D‐glucal is described. Key features of this method are the use of inexpensive reagents in catalytic amounts, mild reaction conditions and an easy workup procedure.magnified image

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.