Tandem Suzuki-Miyaura Coupling/Acid-Catalyzed Cyclization between Vinyl Ether Boronates and Vinyl Halides: A Concise Approach to Polysubstituted Furans

被引：25

作者：

Butkevich, Alexey N. ^{[1
]}

Meerpoel, Lieven ^{[3
]}

Stansfield, Ian ^{[2
]}

Angibaud, Patrick ^{[2
]}

Corbu, Andrei ^{[1
]}

Cossy, Janine ^{[1
]}

机构：

[1] ESPCI ParisTech, CNRS, Chim Organ Lab, F-75231 Paris 05, France

[2] Janssen Res & Dev, Oncol & Med Chem, F-27106 Val De Reuil, France

[3] Janssen Res & Dev, B-2340 Beerse, Belgium

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 15期

关键词：

MULTISUBSTITUTED 2-ACYL FURANS; ONE-POT SYNTHESIS; SUBSTITUTED FURANS; EFFICIENT SYNTHESIS; DERIVATIVES; 1,6-DIOXASPIRO<4.5>DEC-3-ENES; CIS-2-EN-4-YN-1-OLS; SPIROACETALS; ROUTE; ACID;

D O I：

10.1021/ol4014574

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polysubstituted 2-(omega-hydroxyalkyl)furans were prepared by tandem Suzuki-Miyaura coupling/acid-catalyzed cyclization starting from appropriately substituted 3-haloallylic alcohols and dihydrofuran-, dihydropyran- or glycal-derived pinacol boronates.

引用

页码：3840 / 3843

页数：4

共 43 条

[1]

Banerjee R., 2012, INT J REV LIFE SCI, V2, P7

[2] SiO2-Supported CeCl3-7H2O-NaI Lewis acid promoter:: Investigation into the Garcia Gonzalez reaction in solvent-free conditions [J].

Bartoli, Giuseppe ;

Fernandez-Bolanos, Jose G. ;

Di Antonio, Giustino ;

Foglia, Gioia ;

Giuli, Sandra ;

Gunnella, Roberto ;

Mancinelli, Michele ;

Marcantoni, Enrico ;

Paoletti, Melissa .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6029-6036

[3] Determination of the preferred conformation of the bicyclic Galerucella pheromone using density functional theory optimization and calculations of chemical shifts [J].

Bosma, Wayne B. ;

Bartelt, Robert J. ;

Momany, Frank A. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13) :4748-4758

[4] Short and efficient synthesis of chiral furyl carbinols from carbohydrates [J].

Boto, Alicia ;

Hernandez, Dacil ;

Hernandez, Rosendo .

ORGANIC LETTERS, 2007, 9 (09) :1721-1724

[5]

Buechi G., 1968, ORG LETT, V33, P1227

[6] Two-Step One-Pot Synthesis of Benzoannulated Spiroacetals by Suzuki-Miyaura Coupling/Acid-Catalyzed Spiroacetalization [J].

Butkevich, Alexey N. ;

Corbu, Andrei ;

Meerpoel, Lieven ;

Stansfield, Ian ;

Angibaud, Patrick ;

Bonnet, Pascal ;

Cossy, Janine .

ORGANIC LETTERS, 2012, 14 (19) :4998-5001

[7] The first transannular [4+3] cycloaddition reaction: synthesis of the ABCD ring structure of cortistatins [J].

Craft, Derek T. ;

Gung, Benjamin W. .

TETRAHEDRON LETTERS, 2008, 49 (41) :5931-5934

[8] An expedient route to substituted furans via olefin cross-metathesis [J].

Donohoe, Timothy J. ;

Bower, John F. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (08) :3373-3376

[9] New Synthetic Approach for the Construction of Multisubstituted 2-Acyl Furans by the IBX-Mediated Cascade Oxidation/Cyclization of cis-2-En-4-yn-1-ols (IBX=2-Iodoxybenzoic Acid) [J].

Du, Xiangwei ;

Chen, Haoyi ;

Liu, Yuanhong .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (31) :9495-9498

[10] Highly Efficient Synthesis of Multisubstituted 2-Acyl Furans via PIFA/I2-Mediated Oxidative Cycloisomerization of cis-2-En-4-yn-1-ols [J].

Du, Xiangwei ;

Chen, Haoyi ;

Chen, Yifeng ;

Chen, Jingjin ;

Liu, Yuanhong .

SYNLETT, 2011, (07) :1010-1014

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