Gold Catalysis: Switching the Pathway of the Furan-Yne Cyclization

被引：102

作者：

Hashmi, A. Stephen K. ^{[1
]}

Rudolph, Matthias ^{[1
]}

Huck, Juergen ^{[1
]}

Frey, Wolfgang ^{[2
]}

Bats, Jan W. ^{[3
]}

Hamzic, Melissa ^{[1
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany

[2] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

[3] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60439 Frankfurt, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 32期

关键词：

alkynes; arylation; ethers; gold; heterocycles; PHENOL SYNTHESIS; HOMOGENEOUS CATALYSIS; BOND FORMATION; C-C; CYCLOISOMERIZATION; DEAROMATIZATION; COMPLEXES; ALKYNES; ENYNES; TRANSFORMATIONS;

D O I：

10.1002/anie.200900887

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Changing tracks: By the use of alkynyl ethers as directing elements, the furan-yne cyclization enters a new reaction pathway. Instead of phenols, tetracycles containing two heteroatoms and two new stereocenters are formed (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5848 / 5852

页数：5

共 77 条

[1] Gold(I)-catalysed arylation of 1,6-enynes: different site reactivity of cyclopropyl gold carbenes [J].

Amijs, Catelijne H. M. ;

Ferrer, Catalina ;

Echavarren, Antonio M. .

CHEMICAL COMMUNICATIONS, 2007, (07) :698-700

[2]

[Anonymous], ANGEW CHEM

[3]

[Anonymous], ANGEW CHEM

[4]

[Anonymous], 2004, ANGEW CHEM, DOI DOI 10.1002/ANGE.200460232

[5]

[Anonymous], 2007, ANGEW CHEM

[6] Gold catalysis in the reactions of 1,3-dicarbonyls with nucleophiles [J].

Arcadi, A ;

Bianchi, G ;

Di Giuseppe, S ;

Marinelli, F .

GREEN CHEMISTRY, 2003, 5 (01) :64-67

[7] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[8] Asymmetric dearomatization of the furan ring promoted by conjugate organolithimn addition to (menthyloxy)(3-furyl)carbene complexes of chromium [J].

Barluenga, J ;

Nandy, SK ;

Laxmi, YRS ;

Suárez, JR ;

Merino, I ;

Flórez, J ;

García-Granda, S ;

Montejo-Bernardo, J .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (23) :5725-5736

[9] Doubly dearomatising intramolecular coupling of a nucleophilic and an electrophilic heterocycle [J].

Brice, Heloise ;

Clayden, Jonathan .

CHEMICAL COMMUNICATIONS, 2009, (15) :1964-1966

[10] Heterogeneous gold-catalysed synthesis of phenols [J].

Carrettin, Silvio ;

Blanco, M. Carmen ;

Corma, Avelino ;

Hashmi, A. Stephen K. .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (10-11) :1283-1288

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