Palladium Catalyzed Stereoselective C-Glycosylation of Glycals with Enol Triflates

被引:31
作者
Bai, Yaguang [1 ]
Leow, Minli [1 ]
Zeng, Jing [1 ]
Liu, Xue-Wei [1 ]
机构
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore
关键词
BETA-HETEROATOM ELIMINATION; MECHANISTIC INSIGHTS; ARYLBORONIC ACIDS; ARYL IODIDES; STEREOCHEMISTRY; GLYCOSIDATION; AZIRIDINATION; KETONES;
D O I
10.1021/ol202368n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient palladium catalyzed C-glycosylation of glycals with enol triflates has been established. The coupling reactions took place on the anomeric carbon, and the coupling products gave exclusively a isomers. The flexibility of the reaction was exemplified by the broad spectra of substrate scope, constituted of glycals protected with good leaving groups as well as an assortment of enol triflates.
引用
收藏
页码:5648 / 5651
页数:4
相关论文
共 31 条
[1]   SELECTIVE SYMMETRIC AND ASYMMETRIC PALLADIUM-CATALYZED DIMERIZATIONS OF PYRIMIDINYLMERCURIC SALTS [J].
ARAI, I ;
HANNA, R ;
DAVES, GD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (25) :7684-7685
[2]   REGIOSPECIFIC REACTION OF ENOL ETHERS WITH AN ORGANOPALLADIUM SALT - STEREOCHEMICAL AND CONFORMATIONAL EFFECTS ON PRODUCT FORMATION [J].
ARAI, I ;
DAVES, GD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (01) :287-288
[3]   Structure, activity, synthesis and biosynthesis of aryl-C-glycosides [J].
Bililign, T ;
Griffith, BR ;
Thorson, JS .
NATURAL PRODUCT REPORTS, 2005, 22 (06) :742-760
[4]   [3+2] Cycloaddition on Carbohydrate Templates: Stereoselective Synthesis of Pyrrolidines [J].
Cai, Shuting ;
Gorityala, Bala Kishan ;
Ma, Jimei ;
Leow, Min Li ;
Liu, Xue-Wei .
ORGANIC LETTERS, 2011, 13 (05) :1072-1075
[5]   W-7783, A UNIQUE ANTIFUNGAL ANTIBIOTIC [J].
CONNOR, DT ;
GREENOUGH, RC ;
STRANDTMANN, MV .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (23) :3664-3669
[6]   A C-glycosidation approach to the central core of amphidinol 3:: Synthesis of the C39-C52 fragment [J].
de Vicente, J ;
Betzemeier, B ;
Rychnovsky, SD .
ORGANIC LETTERS, 2005, 7 (09) :1853-1856
[7]   ZnCl2/alumina impregnation catalyzed Ferrier rearrangement: an expedient synthesis of pseudoglycosides [J].
Gorityala, Bala Kishan ;
Lorpitthaya, Rujee ;
Bai, Yaguang ;
Liu, Xue-Wei .
TETRAHEDRON, 2009, 65 (29-30) :5844-5848
[8]   A convenient synthesis of pseudoglycosides via a Ferrier-type rearrangement using metal-free H3PO4 catalyst [J].
Gorityala, Bala Kishan ;
Cai, Shuting ;
Lorpitthaya, Rujee ;
Ma, Jimei ;
Pasunooti, Kalyan Kumar ;
Liu, Xue-Wei .
TETRAHEDRON LETTERS, 2009, 50 (06) :676-679
[9]   Bioactive C-glycosides from bacterial secondary metabolism [J].
Hultin, PG .
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2005, 5 (14) :1299-1331
[10]   Microwave-assisted asymmetric intermolecular heck reaction Using phosphine-thiazole ligands [J].
Kaukoranta, Paivi ;
Kallstrom, Klas ;
Andersson, Pher G. .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) :2595-2602