Synthesis of functionalized 2-alkylidene-tetrahydrofurans based on a [3+2]cyclization/bromination/palladium(0) cross-coupling strategy

被引：15

作者：

Bellur, E

Langer, P

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Ernst Moritz Arndt Univ Greifswald, Inst Chem & Biochem, D-17487 Greifswald, Germany

[3] Univ Rostock eV, IfOK, Leibniz Inst Organ Katalyse, D-18059 Rostock, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 22期

关键词：

bromination; cross-coupling; palladium; pyrrolidines; tetrahydrofurans;

D O I：

10.1002/ejoc.200500422

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The bromination of 2-alkylidene-tetrahydrofurans and 2-alkylidene-pyrrolidines - readily available through one-pot [3+2] cyclization reactions - afforded 2-alkylidene-1'-bromotetrahydrofurans, 2-alkylidene-3-bromotetrahydrofurans and 2-alkylidene-1',3-dibromotetrahydrofurans and their pyrrohdine counterparts. 2-Alkylidene-1'-bromotetrahydrofurans were functionalized by performing Suzuki and Heck reactions. 2-Alkylidene-1',3-dibromotetrahydrofurans were successfully employed in novel double-Suzuki reactions. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

引用

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页码：4815 / 4828

页数：14

相关论文

共 47 条

[1] A novel catalytic and highly enantioselective approach for the synthesis of optically active carbohydrate derivatives [J].

Audrain, H ;

Thorhauge, J ;

Hazell, RG ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4487-4497

[2] STUDIES ON THE NACTINS - TOTAL SYNTHESIS OF (+/-)-TERT-BUTYL 8-O-(TERT-BUTYLDIMETHYLSILYL)NONACTATE [J].

BARRETT, AGM ;

SHETH, HG .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) :5017-5022

[3] ENANTIODIVERGENT SYNTHESES OF (+)-NONACTIC AND (-)-NONACTIC ACID AND THE TOTAL SYNTHESIS OF NONACTIN [J].

BARTLETT, PA ;

MEADOWS, JD ;

OTTOW, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (18) :5304-5311

[4] Syntheses and biological evaluation of 3-substituted amino-1-aryl-6-hydroxy-hex-2-ene-1-ones as antioxidant and hypolipidemic agents [J].

Batra, S ;

Srivastava, S ;

Singh, K ;

Chander, R ;

Khanna, AK ;

Bhaduri, AP .

BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (08) :2195-2209

[5]

BELLU RE, 2004, SYNLETT, P2169

[6] Convenient synthesis of ε-halo-β-ketoesters and γ,γ′-dibromoalkanones by regio- and chemoselective reaction of 2-alkylidenetetrahydrofurans with boron trihalides:: A "ring-closure/ring-cleavage" strategy [J].

Bellur, E ;

Langer, P .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :3819-3825

[7] Reaction of 2-alkylidenetetrahydrofurans with boron tribromide: Chemo- and regioselective synthesis of 6-bromo-3-oxoalkanoates by application of a 'cyclization-ring-opening' strategy [J].

Bellur, E ;

Langer, P .

SYNLETT, 2004, (12) :2172-2174

[8] Asymmetric formation of quaternary centers through aza-annulation of chiral β-enamino amides with acrylate derivatives [J].

Benovsky, P ;

Stephenson, GA ;

Stille, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (11) :2493-2500

[9] A NOVEL PYRROLE SYNTHESIS [J].

BERTSCHY, H ;

MEUNIER, A ;

NEIER, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (07) :777-778

[10]

BERTSCHY H, 1990, ANGEW CHEM, V102, P825

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