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

页码：5692 / 5701

页数：10

共 3 条

[1] Chemoselectivity Control: Gold(I)-Catalyzed Synthesis of 6,7-Dihydrobenzofuran-4(5H)-ones and Benzofurans from 1-(Alkynyl)-7-oxabicyclo[4.1.0]heptan-2-ones
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[2] Rh(III)-Catalyzed Cascade Nucleophilic Addition/Annulation of 2-Diazo-1,3-diketones with 1,3-Dicarbonyl Compounds To Access 6,7-Dihydrobenzofuran-4(5H)-ones
Wu, Yinsong
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Li, Ruxue
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JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (11): : 7370 - 7380
[3] Synthesis of 2-Arylimino-6,7-dihydrobenzo[d][1,3] oxathiol-4(5H)-ones via Rh2(OAc)4-Catalyzed Reactions of Cyclic 2-Diazo-1,3-diketones with Aryl Isothiocyanates
He, Xinwei
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ACS OMEGA, 2016, 1 (06): : 1277 - 1283

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