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

• Published in: Chemistry : a European journal Vol. 15; no. 24; pp. 6041 - 6049
• Main Authors: Saquib, Mohammad, Husain, Irfan, Kumar, Brijesh, Shaw, Arun K.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY‐VCH Verlag 08-06-2009
• Subjects: asymmetric synthesis; Catalysis; chiral pool; Chlorides - chemistry; furans; Furans - chemical synthesis; Furans - chemistry; Iodides - chemistry; Lewis acids; Magnetic Resonance Spectroscopy; Molecular Structure; Morita–Baylis–Hillman adducts; Stereoisomerism; Zinc Compounds - chemistry
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.200900007

Enantiopure furan synthesis: A synthesis, catalysed by mixed Lewis acids (ZrCl4/ZnI2), 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.
Simple and efficient syntheses, catalysed by a mixed Lewis acid system (ZrCl4/ZnI2), 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 ZrCl4 and ZnI2 in catalytic amounts.
Enantiopure furan synthesis: A synthesis, catalysed by mixed Lewis acids (ZrCl4/ZnI2), 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.