Emerging Organometallic Methods for the Synthesis of C-Branched (Hetero)aryl, Alkenyl, and Alkyl Glycosides: C-H Functionalization and Dual Photoredox Approaches

被引:65
作者
Ghouilem, Juba [1 ]
de Robichon, Morgane [2 ]
Le Bideau, Franck [1 ]
Ferry, Angelique [2 ]
Messaoudi, Samir [1 ]
机构
[1] Univ Paris Saclay, Fac Pharm, CNRS, BioCIS, F-92290 Chatenay Malabry, France
[2] CY Cergy Paris Univ, BioCIS, CNRS, Equipe Chim Biol, F-95000 Neuville Sur Oise, France
关键词
C-H functionalization; glycosylation; homogeneous catalysis; photochemistry; transition metals; CATALYZED SYNTHESIS; NATURAL-PRODUCTS; ARYL; GLYCOSYLATION; GLYCALS; ARYLATION; ACCESS; DERIVATIVES; ACTIVATION; VITEXIN;
D O I
10.1002/chem.202003267
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Transition-metal-catalyzed C-H functionalization and photoredox nickel dual catalysis have emerged as innovative and powerful avenues for the synthesis of C-branched glycosides. These two concepts have been recently established and provide efficient and mild methods for accessing a series of valuable complex C-branched glycosides of great interest. Herein, recent developments in the synthesis of C-branched aryl/alkenyl/alkyl glycosides through these two approaches are highlighted.
引用
收藏
页码:491 / 511
页数:21
相关论文
共 100 条
[1]   Synthesis and antitumor activities of aquayamycin and analogues of derhodinosylurdamycin A [J].
Acharya, Padam P. ;
Khatri, Hem Raj ;
Janda, Sandip ;
Zhu, Jianglong .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (10) :2691-2704
[2]   Synthesis of Aryl C-Glycosides via Iron-Catalyzed Cross Coupling of Halosugars: Stereoselective Anomeric Arylation of Glycosyl Radicals [J].
Adak, Laksmikanta ;
Kawamura, Shintaro ;
Toma, Gabriel ;
Takenaka, Toshio ;
Isozaki, Katsuhiro ;
Takaya, Hikaru ;
Orita, Akihiro ;
Li, Ho C. ;
Shing, Tony K. M. ;
Nakamura, Masaharu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (31) :10693-10701
[3]   Regio- and Stereospecific Synthesis of C-3 Functionalized Proline Derivatives by Palladium Catalyzed Directed C(sp3)-H Arylation [J].
Affron, Dominic P. ;
Davis, Owen A. ;
Bull, James A. .
ORGANIC LETTERS, 2014, 16 (18) :4956-4959
[4]  
Andrews R.S., 2010, ANGEW CHEM, V122, P7432
[5]   A Photoflow Reactor for the Continuous Photoredox-Mediated Synthesis of C-Glycoamino Acids and C-Glycolipids [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (17) :4140-4143
[6]   Investigating the Rate of Photoreductive Glucosyl Radical Generation [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ORGANIC LETTERS, 2011, 13 (09) :2406-2409
[7]   Intermolecular Addition of Glycosyl Halides to Alkenes Mediated by Visible Light [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7274-7276
[8]  
[Anonymous], 2012, ANGEW CHEM
[9]  
[Anonymous], 2014, ANGEW CHEM, V126, P1282, DOI DOI 10.1002/ANGE.201308016
[10]  
[Anonymous], 2018, Angew. Chem.