Gold-catalyzed synthesis of 2,5-dihydrofurans in ionic liquids

被引：52

作者：

Aksin, Oezge ^{[1
]}

Krause, Norbert ^{[1
]}

机构：

[1] Dortmund Univ Technol, D-44227 Dortmund, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 7-8期

关键词：

allenes; chirality transfer; cycloisomerization; gold catalysis; ionic liquids;

D O I：

10.1002/adsc.200800050

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Nine alpha-hydroxyallenes 1/3 were cyclized to the corresponding 2,5-dihydrofurans 2/4 with complete axis-to-center chirality transfer in the presence of 1 mol% of AuBr3 using [BMIM] [PF6] as solvent at room temperature. The gold catalyst/ionic liquid system is air-stable and recyclable. The leaching of the gold catalyst upon extraction of the product is extremely low (0.03% after five runs).

引用

页码：1106 / 1112

页数：7

共 47 条

[1] Gold-catalyzed synthesis of 2-substituted, 2,3-Disubstituted and 1,2,3-trisubstituted Indoles in [bmim]BF4
Ambrogio, Ilaria
Arcadi, Antonio
Cacchi, Sandro
Fabrizi, Giancarlo
Marinelli, Fabio
[J]. SYNLETT, 2007, (11) : 1775 - 1779
[2] [Anonymous], 2003, CHEM HETEROCYCLES ST, DOI DOI 10.1002/352760183X
[3] Green processing using ionic liquids and CO2
Blanchard, LA
Hancu, D
Beckman, EJ
Brennecke, JF
[J]. NATURE, 1999, 399 (6731) : 28 - 29
[4] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS
BOIVIN, TLB
[J]. TETRAHEDRON, 1987, 43 (15) : 3309 - 3362
[5] Bongers N., 2008, ANGEW CHEM, V120, P2208, DOI DOI 10.1002/ANGE.200704729
[6] Golden opportunities in stereoselective catalysis
Bongers, Nadine
Krause, Norbert
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) : 2178 - 2181
[7] Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans
Buzas, A
Istrate, F
Gagosz, F
[J]. ORGANIC LETTERS, 2006, 8 (09) : 1957 - 1959
[8] Stoichiometric and catalytic reactions of gold utilizing ionic liquids
Deetlefs, M
Raubenheimer, HG
Esterhuysen, MW
[J]. CATALYSIS TODAY, 2002, 72 (1-2) : 29 - 41
[9] A NEW SYNTHETIC ROUTE TO 2,5-DIHYDROFURANS
DULCERE, JP
BARET, N
RODRIGUEZ, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) : 303 - 304
[10] Ionic liquid (molten salt) phase organometallic catalysis
Dupont, J
de Souza, RF
Suarez, PAZ
[J]. CHEMICAL REVIEWS, 2002, 102 (10) : 3667 - 3691

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