Polymer-supported mukaiyama reagent: A useful coupling reagent for the synthesis of esters and amides

被引:53
作者
Crosignani, S [1 ]
Gonzalez, J [1 ]
Swinnen, D [1 ]
机构
[1] Serono Pharmaceut Res Inst, CH-1228 Geneva, Switzerland
关键词
D O I
10.1021/ol0480372
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Polymer-supported N-alkyl-2-chloro pyridinium triflate was synthesized in one step from Wang resin. This reagent proved to be a very effective coupling reagent for the synthesis of esters or amides from carboxylic acids and alcohols or amines (primary and secondary).
引用
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页码:4579 / 4582
页数:4
相关论文
共 17 条
[1]  
AMIN SG, 1979, SYNTHESIS-STUTTGART, P210
[2]   FACILE SYNTHESIS OF CARBOXAMIDES BY USING 1-METHYL-2-HALOPYRIDINIUM IODIDES AS COUPLING REAGENTS [J].
BALD, E ;
SAIGO, K ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1975, (11) :1163-1166
[3]   EXCHANGE REACTIONS OF ALPHA-HALOGENATED PYRIDINES [J].
BRADLOW, HL ;
VANDERWERF, CA .
JOURNAL OF ORGANIC CHEMISTRY, 1951, 16 (07) :1143-1152
[4]   Preparation and evaluation of a polymer-supported Mukaiyama reagent [J].
Convers, E ;
Tye, H ;
Whittaker, M .
TETRAHEDRON LETTERS, 2004, 45 (17) :3401-3404
[5]   Synthesis of carbacephems from serine [J].
Folmer, JJ ;
Acero, C ;
Thai, DL ;
Rapoport, H .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8170-8182
[6]  
Funk RL, 1989, SYNLETT, P36
[7]   AN IMPROVED METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS FROM CARBOXYLIC-ACIDS AND IMINES [J].
GEORG, GI ;
MASHAVA, PM ;
GUAN, XM .
TETRAHEDRON LETTERS, 1991, 32 (05) :581-584
[8]   A CONVENIENT METHOD FOR THE CONSTRUCTION OF BETA-LACTAM COMPOUNDS FROM BETA-AMINO ACIDS USING 2-CHLORO-1-METHYLPYRIDINIUM IODIDE AS CONDENSING REAGENT [J].
HUANG, H ;
IWASAWA, N ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1984, (08) :1465-1466
[9]   N-acylation in combinatorial chemistry [J].
Katritzky, AR ;
Suzuki, K ;
Singh, SK .
ARKIVOC, 2004, :12-35
[10]  
LEY SV, 2000, J CHEM SOC P1, V23, P3815