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

被引：29

作者：

Saquib, Mohammad ^{[1
]}

Husain, Irfan ^{[1
]}

Kumar, Brijesh ^{[2
]}

Shaw, Arun K. ^{[1
]}

机构：

[1] Cent Drug Res Inst, Div Med & Proc Chem, Lucknow 226001, Uttar Pradesh, India

[2] Cent Drug Res Inst, Sophisticated Analyt Instrumentat Facil, Lucknow 226001, Uttar Pradesh, India

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 24期

关键词：

asymmetric synthesis; chiral pool; furans; Lewis acids; Morita-Baylis-Hillman adducts; BIOLOGICAL EVALUATION; SUBSTITUTED FURANS; EFFICIENT; GLYCALS; DIOL; CYCLOISOMERIZATION; METABOLITES; CHEMISTRY; REAGENTS;

D O I：

10.1002/chem.200900007

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：6041 / 6049

页数：9

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