Tandem epoxide or aziridine ring opening by azide/copper catalyzed [3+2] cycloaddition:: Efficient synthesis of 1,2,3-triazolo β-hydroxy or β-tosylamino functionality motif

被引：83

作者：

Kumaraswamy, Gullapalli ^{[1
]}

Ankamma, Kukkadapu ^{[1
]}

Pitchaiah, Arigala ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem 3, Fine Chem Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 25期

关键词：

D O I：

10.1021/jo701724f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[Graphics] A novel and practical procedure for the synthesis of small molecules possessing beta-hydroxy or N-tosylamino 1,2,3-triazole motif by azidation of epoxides or N-tosylaziridines with sodium azide followed by "click reaction" using eco-friendly PEG-400 as a reaction medium in the presence of 5 mol % of CuI is described. Enantiomerically pure epoxide and N-tosylaziridines were afforded in high yield with excellent ee values maintaining complete stereospecificity.

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页码：9822 / 9825

页数：4

相关论文

共 28 条

[11] Expedient synthesis of triazole-linked glycosyl amino acids and peptides [J].

Kuijpers, BHM ;

Groothuys, S ;

Keereweer, AR ;

Quaedflieg, PJLM ;

Blaauw, RH ;

van Delft, FL ;

Rutjes, FPJT .

ORGANIC LETTERS, 2004, 6 (18) :3123-3126

[12] Oppolzer sultam directed aldol as a key step for the stereoselective syntheses of antitumor antibiotic belactosin c and its synthetic congeners [J].

Kumaraswamy, G ;

Padmaja, M ;

Markondaiah, B ;

Jena, N ;

Sridhar, B ;

Kiran, MU .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :337-340

[13] Structurally diverse dendritic libraries: A highly efficient functionalization approach using Click chemistry [J].

Malkoch, M ;

Schleicher, K ;

Drockenmuller, E ;

Hawker, CJ ;

Russell, TP ;

Wu, P ;

Fokin, VV .

MACROMOLECULES, 2005, 38 (09) :3663-3678

[14] Click chemistry en route to pseudo-starch [J].

Marmuse, L ;

Nepogodiev, SA ;

Field, RA .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (12) :2225-2227

[15] HIGHLY ENANTIOSELECTIVE RING-OPENING OF EPOXIDES CATALYZED BY (SALEN)CR(III) COMPLEXES [J].

MARTINEZ, LE ;

LEIGHTON, JL ;

CARSTEN, DH ;

JACOBSEN, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5897-5898

[16] One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from terminal acetylenes and in situ generated azides [J].

Odlo, Kristin ;

Hoydahl, Edmund Andre ;

Hansen, Trond Vidar .

TETRAHEDRON LETTERS, 2007, 48 (12) :2097-2099

[17]

Padwa A., 1984, 1,3-Dipolar Cycloaddition Chemistry, V1

[18]

Prasad A., 2004, ORG LETT, V6, P4223

[19] Towards organo-click chemistry: Development of organocatalytic multicomponent reactions through combinations of Aldol, Wittig, Knoevenagel, Michael, Diels-Alder and Huisgen cycloaddition reactions [J].

Ramachary, DB ;

Barbas, CF .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (21) :5323-5331

[20]

Rostovtsev VV, 2002, ANGEW CHEM INT EDIT, V41, P2596, DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO