Combination of enzyme- and Lewis acid-catalyzed reactions: a new method for the synthesis of 6,7-dihydrobenzofuran-4(5H)-ones starting from 2,5-dimethylfuran and 1,3-cyclohexanediones

被引：8
作者：
Asta, Chimene [1 ]
Schmidt, Dietmar [1 ]
Conrad, Juergen [1 ]
Frey, Wolfgang [2 ]
Beifuss, Uwe [1 ]
机构：
[1] Univ Stuttgart Hohenheim, Inst Chem, D-70599 Stuttgart, Germany
[2] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 34期
关键词：
DYNAMIC KINETIC RESOLUTION; POT CHEMOENZYMATIC SYNTHESIS; DIELS-ALDER REACTION; DOMINO REACTIONS; EFFICIENT SYNTHESIS; FURAN-DERIVATIVES; ORGANIC-SYNTHESIS; REGIOSELECTIVE SYNTHESIS; AMBIENT-TEMPERATURE; SECONDARY ALCOHOLS;
D O I：
10.1039/c3ob40926k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Lewis acid-catalyzed domino 1,2-addition/1,4-addition/elimination between (Z)-3-hexene-2,5-dione and 1,3-dicarbonyls delivers 3-methyl-6,7-dihydrobenzofuran-4(5H)-ones exclusively with yields up to 82%. The combination of this new process with the laccase-catalyzed formation of (Z)-3-hexene-2,5-dione by oxidative cleavage of 2,5-dimethylfuran allows for the synthesis of 6,7-dihydrobenzofuran-4(5H)-ones starting directly from 2,5-dimethylfuran.
引用
收藏
页码：5692 / 5701
页数：10
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