Recyclable Hypervalent-Iodine-Mediated Dehydrogenative α,β′-Bifunctionalization of β-Keto Esters Under Metal-Free Conditions

被引：25

作者：

Duan, Ya-Nan ^{[1
]}

Cui, Li-Qian ^{[1
]}

Zuo, Lin-Hong ^{[1
]}

Zhang, Chi ^{[1
]}

机构：

[1] Nankai Univ, State Key Lab Elementoorgan Chem, Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 37期

基金：

中国国家自然科学基金;

关键词：

AIBX; carbonyl groups; dehydrogenative functionalization; metal-free synthesis; reaction mechanism; ONE-POT SYNTHESIS; UNACTIVATED C(SP(3))-H BONDS; DIPHENYLPROLINOL SILYL ETHER; IODOBENZENE DICHLORIDE; CARBONYL-COMPOUNDS; SODIUM-AZIDE; FUNCTIONALIZED 2,3-DIHYDROFURANS; SEQUENTIAL REACTIONS; SECONDARY ALCOHOLS; MICHAEL ACCEPTORS;

D O I：

10.1002/chem.201502450

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed a method for recyclable hypervalent-iodine-mediated direct dehydrogenative ,- bifunctionalization of -ketoesters and -diketones under metal-free conditions, which affords a straightforward way to synthesize benzo-fused 2,3-dihydrofurans. This efficient, mild method, which has a wide substrate scope and good functional-group tolerance, was used for the multistep synthesis of the protected aglycone of a naturally occurring phenolic glycoside. A mechanism involving Michael addition to an enone intermediate and subsequent oxidative cyclization is proposed.

引用

页码：13052 / 13057

页数：6

共 68 条

[1] Nickel-Catalyzed Direct Arylation of C(sp3)-H Bonds in Aliphatic Amides via Bidentate-Chelation Assistance [J].

Aihara, Yoshinori ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) :898-901

[2]

[Anonymous], 2013, ANGEW CHEM INT, DOI DOI 10.1002/anie.200605192

[3]

Aspin S., 2012, ANGEW CHEM, V124, P10966

[4] Synthesis of Aromatic α-Aminoesters: Palladium-Catalyzed Long-Range Arylation of Primary Csp3-H Bonds [J].

Aspin, Sam ;

Goutierre, Anne-Sophie ;

Larini, Paolo ;

Jazzar, Rodolphe ;

Baudoin, Olivier .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (43) :10808-10811

[5] Phenolic glycosides from Kaempferia parviflora [J].

Azuma, Toshiaki ;

Tanaka, Yasuo ;

Kikuzaki, Hiroe .

PHYTOCHEMISTRY, 2008, 69 (15) :2743-2748

[6] Enantioselective conjugate additions of silylketene acetals to 2-carboxycyclopentenones promoted by chiral Ti complexes [J].

Bernardi, A ;

Karamfilova, K ;

Sanguinetti, S ;

Scolastico, C .

TETRAHEDRON, 1997, 53 (38) :13009-13026

[7]

Burns A.R., 2010, ANGEW CHEM, V122, P5706

[8] Total Synthesis and Structural Reassignment of (+)-Dictyosphaeric Acid A: A Tandem Intramolecular Michael Addition/Alkene Migration Approach [J].

Burns, Alan R. ;

McAllister, Graeme D. ;

Shanahan, Stephen E. ;

Taylor, Richard J. K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) :5574-5577

[9] Functionalized 2,3-dihydrofurans via palladium-catalyzed oxyarylation of α-allyl-β-ketoesters [J].

Cacchi, Sandro ;

Fabrizi, Giancarlo ;

Goggiamani, Antonella ;

Iazzetti, Antonia ;

Madec, David ;

Poli, Giovanni ;

Prestat, Guillaume .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (24) :8233-8236

[10] Boron Trifluoride Etherate Functioning as a Fluorine Source in an Iodosobenzene-Mediated Intramolecular Aminofluorination of Homoallylic Amines [J].

Cui, Jian ;

Jia, Qun ;

Feng, Ruo-Zhu ;

Liu, Shan-Shan ;

He, Tian ;

Zhang, Chi .

ORGANIC LETTERS, 2014, 16 (05) :1442-1445

← 1 2 3 4 5 6 7 →