A room temperature negishi cross-coupling approach to C-alkyl glycosides

被引：138

作者：

Gong, Hegui ^{[1
]}

Sinisi, Riccardo ^{[1
]}

Gagne, Michel R. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 07期

关键词：

D O I：

10.1021/ja068950t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Glycosyl halides serve as effective alkyl halides for room temperature Negishi cross-coupling reactions using functionalized alkyl zinc reagents. The catalyst for these reactions is in situ generated (PyBox)NiCl2. The functional group tolerance on the zinc reagent is typically high, and both benzyl and ester protecting groups on the carbohydrate are tolerated. Anomer selectivities are modest for glucosyl halides but high for mannosyl halides.

引用

页码：1908 / +

页数：3

共 36 条

[1] Evidence for a NiI active species in the catalytic cross-coupling of alkyl electrophiles [J].

Anderson, TJ ;

Jones, GD ;

Vicic, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8100-8101

[2] STABLE GLUCOPYRANOSYLPALLADIUM COMPOUND WITH A CIS-BETA HYDROGEN [J].

ARAI, I ;

DAVES, GD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (25) :7683-7683

[3] IS THERMAL-STABILITY OF SIGMA-ALKYL TRANSITION-METAL COMPLEXES COMPATIBLE WITH THE PRESENCE OF CONFORMATIONALLY FREE BETA-HYDROGENS AND ABSENCE OF STABILIZING LIGANDS - THE ISOLATION OF NOVEL AND UNEXPECTEDLY STABLE 4-MEMBERED CYCLIC (SIGMA-ALKYL)PALLADIUM COMPLEXES [J].

ARNEK, R ;

ZETTERBERG, K .

ORGANOMETALLICS, 1987, 6 (06) :1230-1235

[4] Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides [J].

Arp, FO ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) :10482-10483

[5] A palladium-catalyzed glycosylation reaction: The de novo synthesis of natural and unnatural glycosides [J].

Babu, RS ;

O'Doherty, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12406-12407

[6] Structure, activity, synthesis and biosynthesis of aryl-C-glycosides [J].

Bililign, T ;

Griffith, BR ;

Thorson, JS .

NATURAL PRODUCT REPORTS, 2005, 22 (06) :742-760

[7] Advances in functional-group-tolerant metal-catalyzed alkyl-alkyl cross-coupling reactions [J].

Cárdenas, DJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (04) :384-387

[8] A RAPID SYNTHESIS OF PYRANOID GLYCALS FROM GLYCOSYL BROMIDES [J].

CAVALLARO, CL ;

SCHWARTZ, J .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :7055-7057

[9] Pd-catalyzed ring opening of oxa- and azabicyclic alkenes with aryl and vinyl halides: Efficient entry to 2-substituted 1,2-dihydro-1-naphthols and 2-substituted 1-naphthols [J].

Chen, Chi-Li ;

Martin, Stephen F. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13) :4810-4817

[10] De novo asymmetric bio- and chemocatalytic synthesis of saccharides stereoselective formal O-glycoside bond formation using palladium catalysis [J].

Comely, AC ;

Eelkema, R ;

Minnaard, AJ ;

Feringa, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (29) :8714-8715

← 1 2 3 4 →