N,N,N',N'-TETRAMETHYLAZODICARBOXAMIDE (TMAD), A NEW VERSATILE REAGENT FOR MITSUNOBU REACTION - ITS APPLICATION TO SYNTHESIS OF SECONDARY-AMINES

被引：173

作者：

TSUNODA, T

OTSUKA, J

YAMAMIYA, Y

ITO, S

机构：

来源：

CHEMISTRY LETTERS | 1994年 / 03期

关键词：

D O I：

10.1246/cl.1994.539

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N,N,N,N'-Tetramethylazodicarboxamide, TMAD, was found to be more versatile in the Mitsunobu reaction than traditional diethyl azodicarboxylate or recently developed 1,1'-(azodicarbonyl)dipiperidine, when used in combination with tributylphosphine in benzene. The usefulness of the reagent was demonstrated by the highly efficient two-step synthesis of benzylcrotylamine from N-benzyltrifluoroacetarmide.

引用

收藏

页码：539 / 542

页数：4

相关论文

共 13 条

[1] NITROGEN ACIDS .1. CARBOXAMIDES AND SULFONAMIDES [J].

BORDWELL, FG ;

ALGRIM, D .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (14) :2507-2508

[2] SYNTHESIS AND REACTIONS OF N,N'-DICARBALKOXY-N,N'-DIALKOXYHYDRAZINES AND SOME OBSERVATIONS ON CARBALKOXYLIUM IONS [J].

CRAWFORD, RJ ;

RAAP, R .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (09) :2419-&

[3]

DAUPHIN G, 1961, B SOC CHIM FR, P486

[4] STEREOSPECIFIC SYNTHESIS OF SECONDARY-AMINES BY THE MITSUNOBU REACTION [J].

EDWARDS, ML ;

STEMERICK, DM ;

MCCARTHY, JR .

TETRAHEDRON LETTERS, 1990, 31 (24) :3417-3420

[5] FORMAMOYLATION OF SOME AZO-COMPOUNDS AND CHARACTERIZATION OF REACTION-PRODUCTS [J].

FANTAZIER, RM ;

HERWEH, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (14) :2560-2562

[6]

GOSSELET M, 1975, B SOC CHIM FR II-CH, P249

[7] MITSUNOBU REACTIONS OF N-ALKYL AND N-ACYL SULFONAMIDES - AN EFFICIENT ROUTE TO PROTECTED AMINES [J].

HENRY, JR ;

MARCIN, LR ;

MCINTOSH, MC ;

SCOLA, PM ;

HARRIS, GD ;

WEINREB, SM .

TETRAHEDRON LETTERS, 1989, 30 (42) :5709-5712

[8]

KASHIK TV, 1982, IAN SSSR KH, P2230

[9] ENANTIOSELECTIVE PREPARATION OF 3-SUBSTITUTED-4-PENTENOIC ACIDS VIA THE CLAISEN REARRANGEMENT [J].

KURTH, MJ ;

DECKER, OHW .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5769-5775

[10] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28