A mild, one-pot method for the conversion of carboxylic acids into the corresponding Weinreb amides

被引：23

作者：

Banwell, M ^{[1
]}

Smith, J ^{[1
]}

机构：

[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

SYNTHETIC COMMUNICATIONS | 2001年 / 31卷 / 13期

关键词：

D O I：

10.1081/SCC-100104418

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of various carboxylic acids with N,O-dimethylhydroxylamine under modified Mukaiyama amide coupling conditions affords the corresponding Weinerb amides in generally high yield.

引用

页码：2011 / 2019

页数：9

共 20 条

[1] Convergent synthesis and preliminary biological evaluation of (±)-B-norrhazinal [J].

Banwell, M ;

Edwards, A ;

Smith, J ;

Hamel, E ;

Verdier-Pinard, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (10) :1497-1499

[2] N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters .2. Applications in peptide synthesis. [J].

Barton, DHR ;

Ferreira, JA .

TETRAHEDRON, 1996, 52 (28) :9367-9386

[3] SYNTHESIS OF DISULFIDES VIA SULFENYLATION OF ALKYL AND ARYLDITHIOPYRIDINE N-OXIDES [J].

BARTON, DHR ;

CHEN, C ;

WALL, GM .

TETRAHEDRON, 1991, 47 (32) :6127-6138

[4] THE INVENTION OF RADICAL REACTIONS .15. SOME MECHANISTIC ASPECTS OF THE DECARBOXYLATIVE REARRANGEMENT OF THIOHYDROXAMIC ESTERS [J].

BARTON, DHR ;

BRIDON, D ;

FERNANDEZPICOT, I ;

ZARD, SZ .

TETRAHEDRON, 1987, 43 (12) :2733-2740

[5] EFFICIENT ASYMMETRIC-SYNTHESIS OF INDOLIZIDINE BUILDING-BLOCKS [J].

BOND, TJ ;

JENKINS, R ;

RIDLEY, AC ;

TAYLOR, PC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (19) :2241-2242

[6] PROTECTION OF PRIMARY AMINES AS N-SUBSTITUTED 2,5-DIMETHYLPYRROLES [J].

BRUEKELMAN, SP ;

LEACH, SE ;

MEAKINS, GD ;

TIREL, MD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (12) :2801-2807

[7] A CONVENIENT METHOD FOR THE PREPARATION OF N-METHOXYAMIDES [J].

EINHORN, J ;

EINHORN, C ;

LUCHE, JL .

SYNTHETIC COMMUNICATIONS, 1990, 20 (08) :1105-1112

[8] A NEW MODE OF REACTIVITY OF N-METHOXY-N-METHYLAMIDES WITH STRONGLY BASIC REAGENTS [J].

GRAHAM, SL ;

SCHOLZ, TH .

TETRAHEDRON LETTERS, 1990, 31 (44) :6269-6272

[9] A NEW EFFICIENT SYNTHESIS OF (S)-DOLAPHENINE ((S)-2-PHENYL-1-(2-THIAZOLYL)ETHYLAMINE), THE C-TERMINAL UNIT OF DOLASTATIN-10 [J].

IRAKO, N ;

HAMADA, Y ;

SHIOIRI, T .

TETRAHEDRON, 1992, 48 (35) :7251-7264

[10] SOME UNUSUAL REACTIONS OF WEINREB AMIDES [J].

KECK, GE ;

MCHARDY, SF ;

MURRY, JA .

TETRAHEDRON LETTERS, 1993, 34 (39) :6215-6218

← 1 2 →