N,N′-Ditosylhydrazine:: A convenient reagent for facile synthesis of Diazoacetates

被引：126

作者：

Toma, Tatsuya ^{[1
]}

Shimokawa, Jun ^{[1
]}

Fukuyama, Tohru ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 16期

关键词：

D O I：

10.1021/ol701432k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel entry to the synthesis of diazoacetates is disclosed. A variety of diazoacetates were synthesized from the corresponding bromoacetates by treatment with N,N'-ditosylhydrazine in moderate to high yields. Ease of operation with the stable crystalline reagent as well as a short reaction time offer a useful alternative to the conventional methods.

引用

页码：3195 / 3197

页数：3

共 22 条

[1]

[Anonymous], COMPLETE WORKS

[2] EFFICIENT SYNTHESIS AND INTRAMOLECULAR CYCLOPROPANATION OF UNSATURATED DIAZOACETIC ESTERS [J].

COREY, EJ ;

MYERS, AG .

TETRAHEDRON LETTERS, 1984, 25 (33) :3559-3562

[3] Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion [J].

Davies, HML ;

Beckwith, REJ .

CHEMICAL REVIEWS, 2003, 103 (08) :2861-2903

[4]

Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides

[5] CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].

DOYLE, MP .

CHEMICAL REVIEWS, 1986, 86 (05) :919-939

[6] ELECTRONIC AND STERIC CONTROL IN CARBON HYDROGEN INSERTION REACTIONS OF DIAZOACETOACETATES CATALYZED BY DIRHODIUM(II) CARBOXYLATES AND CARBOXAMIDES [J].

DOYLE, MP ;

WESTRUM, LJ ;

WOLTHUIS, WNE ;

SEE, MM ;

BOONE, WP ;

BAGHERI, V ;

PEARSON, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :958-964

[7] ENANTIOSELECTIVE INTRAMOLECULAR CYCLOPROPANATIONS OF ALLYLIC AND HOMOALLYLIC DIAZOACETATES AND DIAZOACETAMIDES USING CHIRAL DIRHODIUM(II) CARBOXAMIDE CATALYSTS [J].

DOYLE, MP ;

AUSTIN, RE ;

BAILEY, AS ;

DWYER, MP ;

DYATKIN, AB ;

KALININ, AV ;

KWAN, MMY ;

LIRAS, S ;

OALMANN, CJ ;

PIETERS, RJ ;

PROTOPOPOVA, MN ;

RAAB, CE ;

ROOS, GHP ;

ZHOU, QL ;

MARTIN, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5763-5775

[8] PREPARATION AND DECOMPOSITION OF UNSATURATED ESTERS OF DIAZOACETIC ACID [J].

HOUSE, HO ;

BLANKLEY, CJ .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) :53-&

[9] AN ATTEMPTED SYNTHESIS OF PERHYDRO-2-8-METHYLENEPYRIDOCOLINE [J].

JENNINGS, KF .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (MAR) :1172-1175

[10]

Kirmse W, 2002, EUR J ORG CHEM, V2002, P2193

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